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Chemical Structure| 1008-89-5 Chemical Structure| 1008-89-5

Structure of 1008-89-5

Chemical Structure| 1008-89-5

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CAS No.: 1008-89-5

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Product Details of [ 1008-89-5 ]

CAS No. :1008-89-5
Formula : C11H9N
M.W : 155.20
SMILES Code : C1(C2=CC=CC=C2)=NC=CC=C1
MDL No. :MFCD00006280
InChI Key :VQGHOUODWALEFC-UHFFFAOYSA-N
Pubchem ID :13887

Safety of [ 1008-89-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 1008-89-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 49.67
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

12.89 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.63
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.75
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.13
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.52

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.13
Solubility 0.114 mg/ml ; 0.000736 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.55
Solubility 0.436 mg/ml ; 0.00281 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.53
Solubility 0.00462 mg/ml ; 0.0000298 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.38 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.48

Application In Synthesis of [ 1008-89-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1008-89-5 ]

[ 1008-89-5 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 1008-89-5 ]
  • [ 33421-36-2 ]
YieldReaction ConditionsOperation in experiment
75% With oxone; Ru(MesCO2)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride; In 1,2-dichloro-ethane; at 140℃; for 8h;Sealed tube; Green chemistry; General procedure: A mixture of 2-arylpyridines (1 eq), Ru(MesCO2)(L) (p-cymene) [L- 2,2?-bypyridine or 4,4?-dibromobipyridine] (5 mol%), TFA: TFAA=0.6 ml:0.4 ml and Oxone (4 eq) was taken in a 30 ml sealed tube. 1 ml of DCE was added and the tube was then placed in an oil bath, stirred, and heated at 140C. The progress of the reaction was checked after every 8 hrs. After complete consumption of starting material the reaction mixture was cooled to room temperature, quenched with brine and extracted with dichloromethane. The combined organic layer was dried with anhydrous Na2SO4, and vacuum evaporated. The crude product was purified over a column of silica gel (eluent: hexane/ethyl acetate) to afford the desired products.
67% With water; oxygen;copper diacetate; In acetonitrile; at 130℃; for 36h;Product distribution / selectivity; EXAMPLE 1; Synthesis of 2-(pyridine-2-yl)phenol (Ib)In a 20 mL tube, 2-phenylpyridine (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H2O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under * oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 36 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. After purification by column chromatography on silica gel with a gradient eluent of hexane and ether (Rf = 0.35 in 2:1 hexane: ether), the title product was obtained as a colorless oil (34.4 mg, 67%). 1H NMR (400 MHz, CDCl3) delta 14.39 (s, IH), 8.52 (d, J== 4.8 Hz, IH), 7.93 (d, J= 8.4 Hz, IH), 7.87-7.84 (m, IH), 7.81 (d, J= 8.0 Hz, IH), 7.31 (td, J= 7.6, 1.2 Hz, IH), 7.27-7.24 (m, IH), 7.03 (d, J= 8.0 Hz, IH), 6.92 (td, J = 7.6, 1.2 Hz, IH); 13C NMR (100 MHz5 CDCl3) delta 160.29, 158.10, 146.08, 138.05, 131.77, 126.39, 121.79, 119.31, 119.05, 118.89; IR (thin film) v 2923, 1594, 1477, 1270 cm"1; HRMS (TOF) Calcd for CnH10NO (M+ H) 172.0762, found 172.0768.
30% With 18O-labeled water;copper diacetate; In acetonitrile; at 130℃; for 36h;Mechanism; EXAMPLE 6; Labeling ExperimentIn a 20 mL tube, substrate (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H218O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under N2. The <n="42"/>tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 130C for 24 h. The reaction mixture was diluted with 20 mL of CH2CI2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (Rf = 0.35, in 2:1 hexane and ether) to give the product in 30% yield. By the analysis of GC-MS, no I8O-labeled hydroxylated product was detected and only hydroxylated product Ib was obtained.
22% With water; oxygen;copper (II)-fluoride; In dimethyl sulfoxide; at 130℃; for 24h;Product distribution / selectivity; Hydroxylation by CuF 2In a 20 mL tube, substrate (0.3 mmol, 1 equiv), CuF2 (30.5 mg, 0.3 mmol, 1 equiv) andH2O (27 muL, 1.5 mmol, 5 equiv) were dissolved in 1 mL of dry DMSO under atmospheric air. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at1300C for 24 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated <n="39"/>with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (Rf = 0.35 in 2:1 hexane: ether), Ib was obtained as a colorless oil (11.2 mg, 22%).
With tert.-butylhydroperoxide; palladium dichloride; In water; chlorobenzene; at 140℃; for 24h;Green chemistry; To a clean, dry carousel tube, PdCl2 (0.05mmol,8.87mg), 2-phenylpyridine (2mmol,0.286ml), tbutylhydroperoxide (70%solutioninwater, 6mmol, 1.04ml) and chlorobenzene (5mL) were added. The reaction was heated to 140 oC with stirring for 24 h before being cooled to rt. The reaction mixture was filtered through celite and the solvent removed. The crude mixture was then purified by flash column chromatography eluting with dichloromethane to give the phenolic intermediate.

  • 2
  • [ 1008-89-5 ]
  • [ 94928-86-6 ]
  • 3
  • [ 1008-89-5 ]
  • [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
  • [ 94928-86-6 ]
YieldReaction ConditionsOperation in experiment
90.4% In 1,2-dimethoxyethane; at 198 - 200℃; for 1.1h;Microwave irradiation; Inert atmosphere; 300 g of 2-phenylpyridinato, 30.1 g of a chlorine-bridged iridium dimer (D-1) and 3 L of special-grade ethylene glycol were placed in a 6 L separable flask, and the flask was set in a cavity-type microwave irradiation apparatus (SMW-124 manufactured by Shikoku Instrumentation CO., Inc.). An argon gas was blown into the reaction solution for 30 minutes, the reaction solution was thereafter irradiated with a microwave (2450 MHz) at 6 kW while the reaction solution was magnetically stirred, the temperature was elevated from room temperature to a boiling state (around 198° C. to 200° C.) in about 6 minutes, and the reaction solution was further irradiated with a microwave at 6 kW for an hour under an argon atmosphere, and reacted at around 198° C. to 200° C. The reaction solution was cooled to room temperature, and thereafter the reaction solution was filtered to obtain a yellow solid. The yellow solid was washed with methanol, pure water and methanol again, thereafter dried in a vacuum, and recrystallized from a mixed solvent of DMF and methanol to obtain a complex of tris-orthometallated iridium (T-1) described in chemical formula (chemical formula 11) (yield amount: 33.5 g; yield: 90.4percent). The product was analyzed by HPLC (Prominence manufactured by Shimadzu Corporation; detected wavelength: 300 nm), and resultantly found to be a mixture of a facial isomer and a meridional isomer at a ratio of 99.2:0.8 (molar ratio).
85.9% In a Schlenk's flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0. 744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s=10) and 2-phenylpyridine (468 muL, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135°C) for 3 hours. The resulting yellow suspension was cooled to room temperature, to which was added silver (I) trifluoromethanesulfonate (573 mg, 2.232 mmol, 3.0 equivalents), and further stirred at room temperature for 10 minutes to give a dark brown suspension. There was added an additional amount of 2-ethoxyethanol (7 mL, s/s=14) and then dropwise added 2-phenylpyridine (638 muL, 4.464 mmol, 6.0 equivalents), and the mixture was further stirred under refluxing for 3 hours to give an ocher suspension. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and the resulting yellow solid was recrystallized from hexane/dichloromethane to give 837 mg of the title compound (V-i) as yellow powder in 85.9percent yield. 1H NMR (500MHz CD2Cl2) : delta 6.72-6.81 (m, 6H), 6.85-6.93 (m, 6H), 7.56 (ddd, J=0.8, 1.6, 5.5Hz, 3H), 7.62-7.69 (m, 6H), 7.89-7.94 (m, 3H).
83.4% With silver trifluoromethanesulfonate; In 2-ethoxy-ethanol; at 135℃; for 3h;Heating / reflux; In a Schlenk's flask were placed Compound (II-i) (Bis(2-phenylpyridinato-N,C2')iridium(III) chloride dimer) produced in Example 1 (200 mg, 0.187 mmol, 1 equivalent) and silver(I) trifluoromethanesulfonate (144 mg, 0. 561 mmol, 3.0 equivalents), and the interior of the flask was substituted with nitrogen. There were added 2-ethoxyethanol (1 ml, s/s=5) and 2-phenylpyridine (163 muL, 1.122 mmol, 6.0 equivalents), and the mixture was stirred under refluxing (135°C) for 3 hours. The resulting ocher suspension was condensed, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and recrystallized from hexane/dichloromethane to give 208 mg of the title compound (V-i) as yellow powder in 83.4percent yield. NMR data of the product was identical to that of Example 11.
78% Step Two:Added 1200 ml of Ethylene Glycol ether to 3 L of four-neck flask, followed with 18 g of Chlorendic compounds, stirred, Nitrogen gas filled in, then heated and refluxed. When the reflux occurred in the flask, added 12 g of solid sodium carbonate all at once. Dissolved 2-Phenyl Pyridine in 100 ml of Glycerol, and then dripped the mixture in forty minutes by using constant pressure drop funnel. Refluxed with stirring, with sampling interval 1 hour, and 2-3 hours later terminated the reaction. (HPLC: products 95percent-97percent)Cooled the reaction system, added 5.5 L of ethyl acetate, and then rinsed with 4 L.x.3 DI water. Dried the organic phase and concentrated solvent with 200 g of Magnesium Sulfate, and deep yellow solid substances reached. By using Methyl Cyanide, the deep yellow solid substances were recrystallized and 15 g of luminous yellow solid substances with 78percent of yield rate reached.1H-NMR (CDCl3, 400Hz): 7.84 (m, 3H), 7.58 (m, 6H), 7.48 (m, 3H), 6.83 (m, 6H), 6.69 (m, 6H).

  • 4
  • [ 1008-89-5 ]
  • iridium(III) chloride [ No CAS ]
  • [ 94928-86-6 ]
YieldReaction ConditionsOperation in experiment
94% In water; at 205℃; for 48h;Inert atmosphere; Sealed tube; Iridium (III) chloride anhydrous (0.65 g, 2.18 mmol, 1 equiv), 2-phenylpyridine (3.74 mL, 26.1 mmol, 12.0 equiv), and 0.65 L of DI water (0.003 M with respect to IrCl3) is added to a 1 L Parr reactor. The reaction mixture is pressurized with argon (10.0 psi), stirred and then depressurized three times, and finally charged again with argon before sealing. The reaction mixture is heated to 205 °C for 48 h. Then the reactor is cooled to 20 with internal cooling coils. At the end of the experiment the reactor was left in the stand and the contents cooled to 20 °C using cold water. After cooling, the reactor is opened revealing an insoluble yellow solid on the surfaces and dispersed in the aqueous phase. All contents are transferred slowly to a 6 L separatory funnel aided by a large 5 cm glass funnel. Then the interior of the reactor is mechanically scraped (to extract the yellow material), with metal tongs, cotton balls (25 in total), and 500 mL of dichloromethane (DCM) from a spray bottle, and again all contents are added to the separatory funnel. While still in the funnel, the cotton is rinsed with 25 mL of DCM from a spray bottle and evenly pressed with tongs to release the yellow material from the cotton. After removing the cotton, the solution is then diluted with 2.5 L of DCM. The separatory funnel is shaken vigorously, allowed to settle and again shaken, and the organic layer is then slowly separated from the aqueous layer and the aqueous layer is further extracted with more DCM (3 × 10 mL), and the organic layers are combined. The aqueous layers are kept for future ligand recovery. The combined organic layer is washed with a 1 M HCl solution, with vigorous mixing prior to separation (3 × 900 mL). Each HCl wash is then back extracted with DCM (3 × 10 mL) to insure complete recovery of the product. After the final wash, the organic layer is filtered slowly (20 min) through a Celite (35 g) pad on top of a 150 mL medium porosity sintered glass funnel, into a 3 L round-bottomed flask, and then dried with 30 g of MgSO4. After filtering the drying reagent using a 4 L Erlenmyer flask fitted with a 5 cm funnel/cotton plug, a homogenous aliquot is removed for NMR analysis. Finally, the solvent is removed in batches by transferring to a 2.5 L round-bottomed flask by rotary evaporation (35,30 mm Hg, 150 rpm) to afford 1.35 g (94percent) of Ir(ppy)3 as a bright yellow solid.
  • 5
  • [ 1008-89-5 ]
  • iridium(III) acetylacetonate [ No CAS ]
  • [ 94928-86-6 ]
  • 6
  • [ 1008-89-5 ]
  • (C6H3(NO2)CH2N(CH3)2PdOOCCH3)2 [ No CAS ]
  • bis(μ-acetato)bis{(2-(2-pyridyl)phenyl-C1,N)palladium(II)} [ No CAS ]
  • [ 15184-96-0 ]
  • 7
  • [ 1008-89-5 ]
  • iridium(III) chloride hydrate [ No CAS ]
  • [ 94928-86-6 ]
  • 8
  • [ 1008-89-5 ]
  • iridium(III) acetylacetonate [ No CAS ]
  • [ 94928-86-6 ]
YieldReaction ConditionsOperation in experiment
92% With phosphoric acid; In water; glycerol; at 200 - 210℃; for 10h;Heating / reflux;Product distribution / selectivity; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 5.9 g of phosphoric acid (85percent aqueous solution) were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 10 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 2.4 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 92percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.
68 - 85% With tartaric acid; In glycerol; at 200 - 210℃; for 5 - 44h;Heating / reflux;Product distribution / selectivity; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 3.3 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 10 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated with stirring in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 1.8 g of yellow crystals. An MS analysis identified the yellow crystal as tris(2-phenylpyridine)iridium(III) or ortho-metalated iridium complex (2) represented by chemical formula (2): yield, 68percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.; Example 2; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 3.3 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 44 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated with stirring in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 2.2 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 83percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655; .Example 3; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing with N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 9 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 1.8 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 70percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.; Example 4; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 9 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 10 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml ...
60% for 24h; AcetoxyacetoneiridiumIr(acac)3 reacts with C^N bidentate ligand compound 1 for 24 hours.Column-chromatography was used to obtain the electrically neutral light-emitting ring metal iridium complex 2 .The yield is 60percent.
  • 10
  • [ 1008-89-5 ]
  • [ 33421-36-2 ]
  • [ 4253-81-0 ]
  • 11
  • [ 1008-89-5 ]
  • [ 105664-48-0 ]
  • [ 33421-36-2 ]
  • [ 1452876-74-2 ]
  • 12
  • [ 1008-89-5 ]
  • [ 1520-70-3 ]
  • N-(2-(pyridin-2-yl)phenyl)ethanesulfonamide [ No CAS ]
  • 13
  • [ 1008-89-5 ]
  • [ 10421-85-9 ]
  • [ 1271322-37-2 ]
  • 14
  • [ 1008-89-5 ]
  • iridium(III) chloride n-hydrate [ No CAS ]
  • [ 94928-86-6 ]
  • 15
  • [ 1008-89-5 ]
  • [ 94928-86-6 ]
  • C41H29IrN4 [ No CAS ]
  • 16
  • [ 1008-89-5 ]
  • [ 51997-51-4 ]
  • 1-((9H-carbazol-4-yl)oxy)-3-(2-(2-pyridinyl)phenyl)-2-propanol [ No CAS ]
  • 19
  • [ 1008-89-5 ]
  • [ 42019-78-3 ]
  • (4-hydroxyphenyl)(2'-(pyridin-2-yl)biphenyl-4-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; 1-methyl-2-phenyl-3-(diphenylphosphino)-1H-indole; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 24h;Schlenk technique; Inert atmosphere; Sealed tube; General procedure: Two runs were set side by side. A Schlenck tube was loadedwith [RuCl2(p-cymene)]2 (3.1 mg, 5 mol, 1 molpercent), L3 (3.9 mg, 0.01 mmol, 2 molpercent), and K2CO3(173 mg, 1.25 mmol). The tube was backfilled with Ar (3 ×). Under light backflow of Ar, NMP (2.5mL), followed by the required substrate (1a-1d, 1f) (0.6 mmol) and p-chloroanisole (2a; 62 L, 71 mg,0.5 mmol). The tube was sealed and the reaction mixture was stirred at 120 °C for 24 hours. Aftercooling to room temperature, the reaction mixtures from both tubes were combined in H2O (40 mL)and EtOAc (20 mL). The organic phase was separated and washed with H2O (3 × 30 mL), dried(MgSO4), filtered, and concentrated under reduced pressure. The monoarylated products (major) wereisolated after flash chromatography.
  • 20
  • [ 1008-89-5 ]
  • [ 1479-58-9 ]
  • (4-amino-2′-(pyridin-2-yl)[1,1′-biphenyl]-3-yl)(2-fluorophenyl)methanone [ No CAS ]
  • 21
  • [ 1008-89-5 ]
  • [ 50995-48-7 ]
  • C17H18BrNO2 [ No CAS ]
  • 22
  • [ 51169-05-2 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 1008-89-5 ]
  • 23
  • [ 1008-89-5 ]
  • sodium bis(acetylacetonate)dichloroiridium(III) [ No CAS ]
  • [ 94928-86-6 ]
YieldReaction ConditionsOperation in experiment
80% With sodium acetylacetonate; In ethylene glycol; at 180℃; for 17h;Inert atmosphere; 145.3 mg (0.3 mmol) of iridium compound (Ir - 1), 279.0 mg (1.8 mmol) of ligand (L - 1), sodium acetylacetonate hydrate as a beta - diketonate salt, 6 mg (0.75 mmol), and ethylene glycol 2.5 ml were placed in a three-necked flask and reacted under heating in an argon atmosphere at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the yellow solid precipitated was the desired iridium complex (T-1), and the yield was 80percent.
  • 24
  • [ 1008-89-5 ]
  • sodium bis(acetylacetonate)dichloroiridium(III) [ No CAS ]
  • [ 94928-86-6 ]
  • [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71%; 22% In ethylene glycol; at 180℃; for 17h;Inert atmosphere; 145.3 mg (0.3 mmol) of the iridium compound (Ir-1), 279.0 mg (1.8 mmol) of the ligand (L-1), and 2.5 ml of ethylene glycol were placed in a three-necked flask, Under heating at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the yellow solid precipitated was a mixture of (T-1) and (D-1). The yields of (T-1) and (D-1) were calculated to be 71percent and 22percent, respectively, from the integrated value of 1 H-NMR.
  • 25
  • [ 1008-89-5 ]
  • C14H22Cl2IrO4(1-)*K(1+) [ No CAS ]
  • [ 94928-86-6 ]
YieldReaction ConditionsOperation in experiment
87% With sodium acetylacetonate; In ethylene glycol; at 180℃; for 17h;Inert atmosphere; 167.0 mg (0.3 mmol) of iridium compound (Ir - 2), 162.7 mg (1.05 mmol) of ligand (L - 1), 44 sodium acetylacetonate hydrate as beta - diketonate salt, 0 mg (0.36 mmol), and ethylene glycol (2.5 ml) were placed in a three-necked flask and reacted under heating in an argon atmosphere at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the precipitated yellow solid was the desired iridium complex (T-1), and the yield was 87percent.
  • 26
  • [ 1008-89-5 ]
  • C14H22Cl2IrO4(1-)*K(1+) [ No CAS ]
  • [ 94928-86-6 ]
  • [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
22%; 73% In ethylene glycol; at 180℃; for 17h;Inert atmosphere; 167.0 mg (0.3 mmol) of the iridium compound (Ir-2), 162.7 mg (1.05 mmol) of the ligand (L-1), and 2.5 ml of ethylene glycol were placed in a three-necked flask, Under heating at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the yellow solid precipitated was a mixture of (T-1) and (D-1). The yields of (T-1) and (D-1) were calculated to be 22percent and 73percent, respectively, from the integrated value of 1 H-NMR.
  • 27
  • [ 1008-89-5 ]
  • [ 7194-78-7 ]
  • C25H15Br2NO2 [ No CAS ]
  • C18H12BrNO [ No CAS ]
  • 28
  • [ 1008-89-5 ]
  • [ 3297-72-1 ]
  • iridium nitrate [ No CAS ]
  • [ 94928-86-6 ]
  • 1-phenylisoquinoline-bis(phenylpyridine) iridium [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.1%Chromat.; 15.2%Chromat. In water; ethylene glycol; at 180℃; for 17h;Inert atmosphere; 403.8 mg of an iridium nitrate aqueous solution (iridium content: 9.52 wt percent), 93.1 mg of compound (A), 123.2 mg of compound (D) and 5 ml of ethylene glycol were reacted by heating in an argon atmosphere at 180° C. for 17 hours. The reaction mixture was cooled to room temperature, and methanol was added. The precipitated solid was collected by filtration, and washed with methanol. The yield of the resulting solid was 102 mg. Analysis was performed by HPLC (Prominence manufactured by Shimadzu Corporation, column: normal phase silica gel, mobile phase: mixed solvent of THF (40percent) and hexane (60percent), detection wavelength: 300 nm), and the result showed that the production ratios of compounds (1), (34) and (35) were 84.1percent, 15.2percent and 0.7percent (peak area ratio), respectively.
  • 29
  • [ 1008-89-5 ]
  • 4-methyl-2,5-diphenylpyridine [ No CAS ]
  • iridium nitrate [ No CAS ]
  • [ 94928-86-6 ]
  • [ 1215692-67-3 ]
  • [ 1215692-34-4 ]
  • Ir(4-methyl-2,5-diphenylpyridine)<SUB>3</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
17.9%Chromat.; 31.8%Chromat.; 40.6%Chromat.; 9.7%Chromat. In water; ethylene glycol; at 180℃; for 17h;Inert atmosphere; 807.6 mg of an iridium nitrate aqueous solution (iridium content: 9.52 wt percent), 124 mg of compound (A), 98 mg of compound (I) and 5 ml of ethylene glycol were reacted by heating in an argon atmosphere at 180° C. for 17 hours. The reaction mixture was cooled to room temperature, and then extracted with dichloromethane added thereto. The organic extract was concentrated under reduced pressure, and from the precipitated solid, origin impurities were removed by silica gel chromatography (eluant: dichloromethane). The yield of the solid obtained after purification was 196 mg. Analysis was performed by HPLC (Prominence manufactured by Shimadzu Corporation, column: normal phase silica gel, mobile phase: mixed solvent of THF (40percent) and hexane (60percent), detection wavelength: 300 nm), and the result showed that the production ratios of compounds (1), (37), (38) and (39) were 17.9percent, 40.6percent, 31.8percent and 9.7percent (peak area ratio), respectively.
  • 30
  • [ 1008-89-5 ]
  • [ 1064194-10-0 ]
  • tert-butyl 3-(2-(pyridin-2-yl)phenyl)azetidine-1-carboxylate [ No CAS ]
  • 31
  • [ 1008-89-5 ]
  • [ 33421-36-2 ]
  • [ 1452876-54-8 ]
 

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