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Chemical Structure| 10485-09-3 Chemical Structure| 10485-09-3

Structure of 10485-09-3

Chemical Structure| 10485-09-3

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CAS No.: 10485-09-3

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Product Details of [ 10485-09-3 ]

CAS No. :10485-09-3
Formula : C9H7Br
M.W : 195.06
SMILES Code : C1=CC=CC2=C1C=C(Br)C2
MDL No. :MFCD06797863
InChI Key :CCUYEVNCRQDQRF-UHFFFAOYSA-N
Pubchem ID :575586

Safety of [ 10485-09-3 ]

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

Computational Chemistry of [ 10485-09-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 47.25
TPSA ?

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

0.0 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

2.34
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

3.12
Log Po/w (WLOGP)?

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

2.87
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.

3.23
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

3.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.99

Water Solubility

Log S (ESOL):?

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

-3.46
Solubility 0.0678 mg/ml ; 0.000348 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.

-2.79
Solubility 0.317 mg/ml ; 0.00163 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

-3.83
Solubility 0.0286 mg/ml ; 0.000147 mol/l
Class?

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

Soluble

Pharmacokinetics

GI absorption?

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

 Low
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

 No
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.

-5.27 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)

 2.69

Application In Synthesis of [ 10485-09-3 ]

* 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 [ 10485-09-3 ]

[ 10485-09-3 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 5400-80-6 ]
  • [ 10485-09-3 ]
YieldReaction ConditionsOperation in experiment
77% With H-β-zeolite; In chlorobenzene; at 120℃; for 6h; General procedure: In a 25 mL round bottomed flask, 250 mg (1.2 mmol) of 2-bromo-1-phenylethanol (1a), 50 mg (20 W/W %) H-β-Zeolite and 1.0 mL of chlorobenzene were placed. The reaction flask was placed in an oil bath at 120C for 6 h; the progress of the reaction was monitored by TLC. After completion of the reaction, the flask was allowed to attain room temperature, and filtered through Watt-Mann filter paper and washed with 10 mL of diethyl ether. Removal of the solvent under reduced pressure, the left out residue was purified by column chromatography on silica gel (200-400 mesh) and hexane as eluent to obtain 2a in (0.16 g) 72% yield.
70% With toluene-4-sulfonic acid; In toluene; at 90℃; for 20h; (2) Synthesis of 2-bromoindene 25 g was taken from the bromohydrin compound obtained from the above reaction, dissolved in 300 mL of toluene, then 500 mg of p-toluene sulfonic acid was added thereto, and the temperature was raised to 90 C., and stirring was carried out for 20 h. After the reactant was cooled to room temperature, it was washed with a sufficient amount of water, dehydrated with MgSO4, and filtered and dried under reduced pressure, thereby obtaining a brown concentrate. This was dissolved in about 100 mL of hexane, and hexane was filtered as an eluent through a silica pad, thereby obtaining non-viscous yellow oil (2-bromoindene) in a yield of 60 to 70%. 1H NMR (500 MHz, CDCl3): δ 3.61 (3H, s), 6.95 (1H, s), 7.18-7.20 (3H, m), 7.27-7.32 (1H, m), 7.39 (1H, m)
60% toluene-4-sulfonic acid; In toluene; for 24h;Heating; Indene (259 mmol, 30 g) and distilled water (9 mL) were put into dimethyl sulfoxide (DMSO, 90 mL), the temperature was decreased to 0C, and N-bromosuccinimide (NBS, 263 mmol, 46.9 g) was slowly added thereto. The temperature of this solution was increased to normal temperature, and the solution was agitated for 12 hours. After that, after the reaction was finished by distilled water, the organic layer was extracted with diethyl ether, and moisture was removed by anhydrous magnesium sulfate. After the filtration under reduced pressure, compound B (38.9 g, 72%) was obtained by removing the solvent by reducing the pressure of the filtered solution and recrystallizing the solution by hexane. 14.3 g of compound B and p-toluenesulfonic acid (p-TsOH, 2.6 mmol, 0.5 g) were dissolved in 60 mL of toluene, and agitated and heated for 24 hours while water was removed by using the Tin-Stock method. Compound C (7.8 g, 60%) was obtained by decreasing the temperature of the solution to normal temperature and using the fractionation method.
40.6 g (88.7%) With p-toluenesulfonic acid monohydrate; In chloroform; toluene; Preparation of 2-Bromoindene To a 500 mL flask containing a magnetic stir bar was added (+/-)trans-2-bromo-1-indanol (50.0 g, 235 mmol), p-toluenesulfonic acid monohydrate (0.50 g, 2.6 mmol), and toluene (300 mL). A Dean Stark trap and reflux condenser were placed on the flask, and the reaction was refluxed for 16 hours. The reaction was transferred to a separatory funnel, chloroform was added (200 mL), and the resulting mixture was washed with aqueous sodium bicarbonate solution (3*200 mL). The organic layer was then washed with a saturated aqueous sodium chloride solution (1*300 mL), dried over anhydrous magnesium sulfate, and filtered. The solvents were removed and distillation provided 40.6 g (88.7 percent) of the slightly yellow crystalline solid collected at 72-105 C. at 3 mm Hg. 1 H NMR (300 MHz, CDCl3, TMS); δ7.4-7.1(m, 4H), 6.93(s, 1H), 3.60(s, 2H). 13 C NMR (75 MHz, CDCl3): δ143.62, 142.22, 132.64, 126.38, 124.59, 124.49, 122.85, 119.88, 45.40. GC-MS: Calculated for C9 H7 79 Br 193.97, found 194.00. Calculated for C9 H7 81 Br 195.90, found 195.90.
With toluene-4-sulfonic acid; In toluene; for 12h;Inert atmosphere; Schlenk technique; Reflux; To a mixture of indene (200mmol), distilled water (15ml) and dimethyl sulfoxide (70ml) was added portion wise an amount of 210mmol of N-bromosuccinimide. The resulting orange solution was stirred for 10h at room temperature, hydrolyzed with chilled water (100ml), and extracted with diethyl ether (3×100ml). The combined extracts were dried with magnesium sulphate and concentrated to give crystals of 2-bromoindan-1-ol upon standing overnight at -24C. The obtained 2-bromoindan-1-ol (120mmol) was suspended in 100ml of toluene and mixed with a catalytic amount of para-toluenesulfonic acid monohydrate. The mixture was heated at reflux for 12h, and water was removed by a Dean-Stark apparatus. The resulting dark brown suspension was filtered and the volatiles were removed under vacuum. The residue was passed through silica gel using pentane as eluent, then the solvent was evaporated, and the crude product was distilled in vacuo. 2-Bromoindene was finally obtained as yellow crystals in 55% yield.

  • 2
  • [ 10485-09-3 ]
  • [ 13291-18-4 ]
  • [ 38740-43-1 ]
  • 3
  • [ 10485-09-3 ]
  • [ 67300-99-6 ]
  • 2-(1-phenylvinyl)-1H-indene [ No CAS ]
  • 4
  • [ 10485-09-3 ]
  • [ 94012-71-2 ]
  • [ 902759-00-6 ]
  • 5
  • [ 10485-09-3 ]
  • [ 1692-25-7 ]
  • 3-(1<i>H</i>-inden-2-yl)-pyridine [ No CAS ]
  • 6
  • [ 22385-77-9 ]
  • [ 10485-09-3 ]
  • [ 218604-62-7 ]
  • 7
  • [ 110-18-9 ]
  • [ 10485-09-3 ]
  • C9H7Br(1-)*2C6H16N2*Li(1+) [ No CAS ]
  • 8
  • [ 928118-99-4 ]
  • [ 10485-09-3 ]
  • [ 787-61-1 ]
YieldReaction ConditionsOperation in experiment
54% With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h;Reflux; 1.2 g (6.2 mmol) of <strong>[10485-09-3]2-bromoindene</strong>, 3.4 g (8.4 mmol) of tributyl-(1H-inden-2-yl)-stannane, 0.44 g (0.63 mmol) of (PPh3)2PdCl2, and 70 mL of THF were refluxed for 24 hours. Then the reaction was added with water and extracted with ethyl acetate for 3 times. The organic layers were combined and dried with anhydrous MgSO4. The solvent was removed by rotary vacuum evaporator and the residue was purified by silica gel chromatography (hexane/dichloromethane = 10/1) to afford 2,2’-biindene (0.79g, 3.4 mmol, 54% yield).
  • 9
  • [ 10485-09-3 ]
  • 2-(tributylstannyl)benzothiophene [ No CAS ]
  • 2-(2'-indenyl)benzothiophene [ No CAS ]
  • 10
  • [ 10485-09-3 ]
  • [ 75-78-5 ]
  • bis(2-indenyl)dimethylsilane [ No CAS ]
  • 1,2'-2,1'-[bis(dimethylsilyldiyl)]bisindene [ No CAS ]
  • 11
  • [ 10485-09-3 ]
  • [ 75-78-5 ]
  • bis(2-bromo-3H-indenyl)dimethylsilane [ No CAS ]
  • 12
  • [ 29786-93-4 ]
  • [ 10485-09-3 ]
  • (2-bromoindenyl)lithium [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In hexanes; at -30 - 20℃; for 20.1667h; In the Glove Box, 32.0 ml of 1.6 M "BuLi (51.2 mmol) in hexanes were added dropwise for 10 min at -3O0C to a solution of 10.0 g (51.3 mmol) of 2- bromoindene in 220 ml of hexanes. This mixture was stirred for 20 h at ambient temperature. The precipitate that formed was filtered off, washed with 3 x 50 ml of hexanes, and dried in vacuum. This procedure gave 7.92 g (77%, 39.4 mmol) of the lithium salt of <strong>[10485-09-3]2-bromoindene</strong>, which was then added at -1000C to a suspension of 4.59 g (19.7 mmol) of ZrCl4 in 200 ml of CH2Cl2. The reaction mixture was slowly warmed for 1 h to 2O0C and, then, stirred for 24 h at ambient temperature. The resulting mixture was filtered through Celite 503 and the filtrate was evaporated to about 70 ml. Crystals that precipitated at -3O0C were separated, washed with 3 x 20 ml of cold hexanes, and dried in vacuum. Yield 11.2 g (52%) of a yellow crystalline product.Anal. calc. for C18H12Br2Cl2Zr: C, 39.29; H, 2.20. Found: C, 39.67; H, 2.39.1H NMR (CD2Cl2): δ 7.46 (dd, J= 6.6 Hz, J= 3.2 Hz, 4H, 4,4',7,7'-H), 7.19 (dd, J= 6.6 Hz, J= 3.2 Hz, 4H, 5,5',6,6'-H), 6.48 (s, 4H, 1,1',3,3'-H).13C NMR (CD2Cl2): δ 128.4, 127.8, 125.9, 110.1, 107.4.
  • 13
  • [ 10485-09-3 ]
  • [ 2633-66-1 ]
  • [ 749870-00-6 ]
YieldReaction ConditionsOperation in experiment
68% tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In tetrahydrofuran; at 20℃; for 48h; A mixture of 50.0 ml (20.0 mmol) of 0.4 M mesitylmagnesium bromide in THF, 230 mg (0.40 mmol) of Pd(dba)2, 162 mg (0.80 mmol) of P^Bu3, and 3.90 g (20.0 mmol) of 2-bromo-lH-indene was stirred for 48 h at ambient temperature. Then, to the resulting mixture 200 ml of brine was added. The organic layer was separated, and the aqueous layer was extracted with 3 x 100 ml of ether. The combined organic fractions were dried over K2CO3 and then evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 urn, d 30 mm, 1 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.). Yield 3.19 g (68%) of white solid.Anal. calc. for C18H18: C, 92.26; H, 7.74. Found: C, 92.33; H, 7.73.1H NMR (CDCl3): δ 7.52 (m, IH, 7-H in indenyl), 7.46 (m, IH, 4-H in indenyl), 7.35 (m, IH, 6-H in indenyl), 7.24 (m, IH, 5-H in indenyl), 6.97 (s, 2H, 3,5-H in mesityl), 6.68 (m, IH, 3-H in indenyl), 3.60 (m, 2H, CH2), 2.36 (s, 3H, 4- Me in mesityl), 2.22 (s, 6H, 2,6-Me in mesityl).
  • 14
  • [ 10485-09-3 ]
  • [ 556-63-8 ]
  • [ 41712-14-5 ]
  • 15
  • [ 10485-09-3 ]
  • [ 947617-22-3 ]
  • bis-2-indenyl-1,8-naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% The synthesis of the naphthyl ligand is shown in scheme 2. <strong>[10485-09-3]2-bromoindene</strong> (6.66 g, 0.0342 moles) was taken in a round-bottomed flask and dissolved in toluene. Tetrakis triphenyl phosphine palladium (0.054gm, 8mol%) was added to the above solution and stirred for 10-15 min. To this solution the diboronic acid from step 1 (3g, 0.0156 moles) dissolved in ethanol (5ml) was added, followed by aqueous sodium carbonate (2M, 10ml). The reaction mixture was heated to 80C and stirred for 24hrs. It was cooled and extracted with dichloromethane (DCM; 5 x 50ml). The DCM portion was then extracted with water (2 x 50ml), dried over sodium sulfate and concentrated. The crude compound was purified by column chromatography by continuously eluting with hexane as the eluent. Crude yield = 3g; Purified yield = 1.6g (33%)
  • 16
  • [ 10485-09-3 ]
  • [ 5720-06-9 ]
  • 2-(o-methoxyphenyl)indene [ No CAS ]
  • 17
  • [ 10485-09-3 ]
  • [ 118062-05-8 ]
  • 2-(2,3,4-trimethoxyphenyl)-1H-indene [ No CAS ]
  • 18
  • [ 10485-09-3 ]
  • [ 94839-07-3 ]
  • 5-(1H-2-indenyl)-1,3-benzodioxol [ No CAS ]
  • 19
  • [ 10485-09-3 ]
  • (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1H-indene-2-yl)methyl-6-methoxy]phenyl]-D-glucitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
(Example 74) 1,2-Dibromoethane (one drop) was added to a solution of zinc dust (86 mg) in tetrahydrofuran (2.0 ml) in an argon atmosphere, and the solution was refluxed for five minutes. Chlorotrimethylsilane (a drop) was added to the mixture at room temperature, and the mixture was stirred for 15 minutes. Then, (1S)-2,3,4,6-tetra-0-acetyl-1,5-anhydro-1-(3-bromomethyl -6-methoxy)phenyl-D-glucitol (700 mg) was added to the mixture, and the mixture was refluxed for one hour. <strong>[10485-09-3]2-bromo-1H-indene</strong> (128 mg) and tetrakistriphenylphosphine palladium (76 mg) were added to the mixture, and the mixture was heat-refluxed for five hours. The temperature of the mixture was cooled to room temperature, and aqueous solution of saturated ammonium chloride was added. The insoluble matter was separated by filtration, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue, and the residue was purified by silica gel column chromatography (chloroform-ethyl acetate) to obtain (1S)-2,3,4,6-tetra-0-acetyl-1,5-anhydro-1-[3-[(1H-indene -2-yl)methyl-6-methoxy]phenyl]-D-glucitol (190 mg). The compounds in Examples 75 to 79 were obtained in a manner similar to that of Example 74.
  • 20
  • [ 10485-09-3 ]
  • [ 2234-82-4 ]
  • [ 92013-11-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;Ni(dppp)Cl2; In diethyl ether; Preparation of 2-Propylindene To an oven-dried 250 mL round bottom flask containing a magnetic stir bar and equipped with a reflux condenser and vacuum adapter was added <strong>[10485-09-3]2-bromoindene</strong> (15.0 g, 76.9 mmol) and Ni(dppp)Cl2 (0.42 g, 0.77 mmol) (dppp=1,3-bis(diphenyl-phosphino)propane). The flask was stoppered and evacuated. Deoxygenated anhydrous diethyl ether (150 mL) was added via cannula under argon at -78 C. The reaction was stirred under argon without exterior cooling as 42 mL of a 2.0 M propylmagnesium chloride in ether solution was added via syringe (84 mmol propylmagnesium chloride). The reaction was placed in a dry ice/acetone bath when a vigorous reflux was achieved. The dry ice/acetone bath was removed after 2 minutes, and the reaction was stirred at room temperature under argon for 90 minutes. The reaction was carefully poured into water and 10 weight percent aqueous HCl was added until the mixture was acidic. The mixture was extracted with ether (3*200 mL), and the combined organic layers were washed with water (1*250 mL), with aqueous sodium bicarbonate (1*250 mL), and with aqueous saturated sodium chloride solution (1*250 mL). Drying over anhydrous sodium sulfate followed by filtration and solvent removal yielded 12.14 g (99.7 percent) of the desired product. 1 H NMR (300 MHz, CDCl3, TMS): δ7.4-7.0 (m, 4H), 6.48 (s, 1H), 3.26 (s, 2H), 2.43 (t, 3 JHH =7.4 Hz, 2H), 1.61 (s, 3 JHH =7.4 Hz, 2H), 0.96 (t, 3 JHH =7.4 Hz, 3H). 13 C NMR (75 MHz, CDCl3), δ150.17, 145.46, 142.83, 126.03, 125.96, 123.30, 123.10, 119.64, 40.81, 33.23, 22.15, 13.95. GC-MS: Calculated for C12 H14 158.11, found 158.05.
  • 21
  • [ 10485-09-3 ]
  • [ 17059-50-6 ]
YieldReaction ConditionsOperation in experiment
93.1% Ni(dppp)Cl2; In diethyl ether; Preparation of 2-Ethylindene 2-Bromoindene (8.1235 g, 0.04211 moles) and Ni(dppp)Cl2 (0.1536 g, 2.83*10-4 moles) were stirred in diethylether (100 mL) at -78 C. under a nitrogen atmosphere as ethylMgBr (0.045 moles, 15.00 mL of 3.0 M solution in diethylether) was added. The dry-ice bath was then removed and the reaction mixture allowed to warm to room temperature. The reaction mixture started off as a heterogeneous brick-red color and then turned to a homogeneous yellow/gold solution and then back to the heterogeneous brick-red mixture during the course of the warm-up. Gas chromatographic analysis after 2 hours of stirring at room temperature showed that the reaction was substantially quantitative. After the reaction period the mixture was poured onto ice and then extracted with 1 M HCL (1*100 mL) and 1 M NaHCO3 (1*100 mL) and then dried with MgSO4 and filtered. The desired product was isolated as a light yellow oil (5.65 g, 93.1 percent). 1 H NMR (300 MHz, CDCl3, TMS): δ1.31 (t, 3 JHH =7.4 Hz, 3H), 2.59 (q, 3 JHH =7.4 Hz, 2H), 3.39 (s, 2H), 6.59 (s, 1H), 7.16-7.38 (m, 3H), 7.46 (d, 3 JHH =7.4 Hz, 1H). 13 C NMR (75 MHz, CDCl3): δ13.65, 24.63, 41.23, 119.96, 123.47, 123.60, 125.25, 126.29, 143.12, 145.76, 152.47. GC-MS: Calculated for C11 H12 144.22, found 144.10.
  • 22
  • [ 10485-09-3 ]
  • [ 2177-47-1 ]
YieldReaction ConditionsOperation in experiment
Ni(dppp)Cl2; In diethyl ether; Preparation of 2-Methylindene via 2-Bromoindene 2-Bromoindene (24.4 g, 0.125 moles) and Ni(dppp)Cl2 (0.925 g, 1.71*10-3 moles) (dppp=1,3-bis(diphenyl-phosphino)propane) were stirred in diethylether (200 mL) at -78 C. under a nitrogen atmosphere as methylMgBr (0.150 moles, 50.00 mL of 3.0 M solution in diethylether) was added. The dry-ice bath was then immediately removed and the reaction mixture allowed to warm to room temperature. The reaction mixture started off as a heterogeneous brick-red color and then turned to a homogeneous yellow/gold solution. After an hour of stirring in this state an exotherm occurred which resulted in some refluxing of the ether in the flask. The solution then turned back to the heterogeneous brick-red mixture. Total stirring time for the mixture was 3 hours following the removal of the ice-bath after which time GC analysis showed that the conversion of <strong>[10485-09-3]2-bromoindene</strong> to 2-methylindene was substantially quantitative. After the reaction period the mixture was poured onto ice and then extracted with 1 M HCL (1*100 mL) and 1 M NaHCO3 (1*100 mL) and then dried with MgSO4 and filtered.
  • 23
  • [ 10485-09-3 ]
  • [ 106-93-4 ]
  • [ 75-78-5 ]
  • 2-chloromethylsilylindene [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran; (Production example 1) Synthesis of (dimethylsilylene) 2 (indene) 2 Under nitrogen flow, a 1L three-necked flask receives 50 mL of THF and 2.5 g (41 mmol) of Mg. To this 0.1 mL of 1,2-dibromoethane is added and the mixture is stirred to activate Mg. After stirring for 30 minutes, the solvent is removed and 50 mL of THF is newly added. To this, a solution of 5.0 g (25.6 mmol) of <strong>[10485-09-3]2-bromoindene</strong> in THF (200 mL) is added dropwise over 2 hours. After completion of the addition followed by stirring at room temperature for 2 hours followed by cooling to -78C, a solution of 3.1 mL (25.6 mmol) of dichlorodimethylsilane in THF (100 mL) is added dropwise over 1 hour. After stirring for 15 hours, the solvent is evaporated off. The residue was extracted with 200 mL of hexane and the solvent was distilled off to obtain 6.6 g (24.2 mmol) of 2-chloromethylsilylindene (yield: 94%).
  • 24
  • [ 22385-77-9 ]
  • [ 10485-09-3 ]
  • [ 594-19-4 ]
  • [ 218604-62-7 ]
YieldReaction ConditionsOperation in experiment
70% With magnesium bromide diethyl etherate; In pentane; 2-(3,5-Di-t-butylphenyl)indene (Ligand D) 1-Bromo-3.5-di-t-butylbenzene (47.2g, 0.175 mol) was dissolved in ether (500 mL) and cooled to -70C. t-Butyllithium (200 mL of 1.7 M solution in pentane, 0.34 mol) was added at -70C over a two-hour period. The solution was allowed to warm to room temperature slowly. Magnesium bromide etherate (46.5g. 0.18 mol) was added and the slurry was stirred for one hour. The mixture was then cooled to 5C and <strong>[10485-09-3]2-bromoindene</strong> (34.2 g, 0.18 mol) was added. The mixture was warmed to room temperature and then refluxed for three hours. The solution was cooled to room temperature and the reaction was quenched carefully with water. The layers were separated and the organics washed with salt brine and dried over magnesium sulfate. The solvents were evaporated and the product was distilled twice and recrystallized from hexane to give 37.1 g of product (70% yield).
  • 25
  • [ 288-32-4 ]
  • [ 10485-09-3 ]
  • [ 886040-05-7 ]
YieldReaction ConditionsOperation in experiment
63% With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In 1,4-dioxane; at 110℃; for 24h; (1) Synthesis of Compound 1 Compound 1 as the intermediate compound to Compound 2 shown in the following was synthesized as described in the following. The reaction was conducted entirely under a stream of argon gas. Into 40 ml of dioxane, 0.380 g (0.05 eq; the molecular weight: 190.45; 2.00×10-3 moles) of copper(I) iodide, 0.720 g (0.1 eq; the molecular weight: 180.21; 4.00×10-3 moles) of 1,10-phenanthroline and 27.4 g (2.1 eq; the molecular weight: 325.82; 0.084 moles) of cesium carbonate were suspended. To the resultant suspension, 7.80 g (1 eq; the molecular weight: 195.06; 4.00×10-2 moles) of <strong>[10485-09-3]2-bromoindene</strong> and 3.27 g (1.2 eq; the molecular weight: 68.08; 4.80×10-2 moles) of imidazole were added, and the obtained mixture was heated under the refluxing condition at 110 C. for 24 hours. When the reaction was completed, the temperature was reduced to the room temperature. To the cooled mixture, about 200 ml of methylene chloride was added, and the resultant mixture was filtered while being passed through Celite. The solvent was removed from the filtrate under a reduced pressure, and 4.59 g (the molecular weight 182.22; 0.0252 moles; the yield: 63%) of Intermediate compound A was separated from the obtained residue in accordance with the column chromatography (the developing solvent: methylene chloride).
  • 26
  • [ 10485-09-3 ]
  • [ 536-74-3 ]
  • [ 23909-36-6 ]
  • 27
  • [ 5419-55-6 ]
  • [ 10485-09-3 ]
  • C15H21BO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Under an atmosphere of argon, magnesium turnings (0.86 g, 35 mmol) covered with dry THF (5 ml_) were activated with a few drops of 1, 2 - dibromoethane. To the <n="87"/>solution of activated magnesium turnings was added dropwise a solution of 2-bromo- 1H-indene (3.45 g, 17.7 mmol) in dry THF (20 mL). The reaction was stirred at room temperature for 2 hours, then the reaction mixture was added via syringe to a -80 C solution of tri-isopropoxy-borane (4.6 mL, 20 mmol) in dry THF (10 mL). The resulting reaction was allowed to warm to room temperature on its own and was stirred for 16 hours. The reaction mixture was quenched with ice and acidified with HCI, then extracted with ether (3 x 15 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel (40% ethyl acetate/hexanes) to provide compound 17A.
  • 28
  • [ 10485-09-3 ]
  • [ 920-39-8 ]
  • [ 57653-14-2 ]
YieldReaction ConditionsOperation in experiment
71.1% Under an argon atmosphere, a solution of zinc chloride g, 28.0 mmol) in tetrahydrofuran suspension (5 mL) was added with a solution of isopropyl magnesium bromide in tetrahydrofuran (0.78 M, 30.7 mL) at 0 C., and the resultant was stirred at the same temperature for 1 hour. Then a solution of tetrakistriphenyl phosphine palladium (800 mg, 0.70 mmol) and <strong>[10485-09-3]2-bromoindene</strong> (3.87 g, 20.0 mmol) in tetrahydrofuran (10 mL) was added thereto, and the resultant was further stirred at the same temperature for 16 hours. The reaction solution was added with a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the resultant residue was purified using silica-gel chromatography (hexane). 2-Isopropylindene (2.25 g, 71.1%) was obtained as a colorless oil.1H-NMR (400 MHz, CDCl3) δ; 1.22 (d, J=6.6 Hz, 6H), 2.77 (septet, J=6.6 Hz, 1H), 3.30 (s, 2H), 6.50 (s, 1H), 7.10-7.34 (m, 4H).
  • 29
  • [ 19756-04-8 ]
  • [ 2857-97-8 ]
  • [ 10485-09-3 ]
  • [ 892576-01-1 ]
YieldReaction ConditionsOperation in experiment
66% To a solution of 9.49 g (48.7 mmol) of 2-bromo-lH-indene in 490 ml of ether, 12.3 g (46.3 mmol) of Zr(NMe2)4 was added. The reaction mixture was stirred for 12 h and then evaporated to dryness. The residue was dissolved in 500 ml of toluene, and 23.1 g (151 mmol) of bromotrimethylsilane was added. The mixture was stirred for 24 h at room temperature, evaporated to a volume equal to ca. 250 ml, and filtered through a glass frit (G4). Crystals that precipitated at a temperature of 3O0C from the filtrate were separated, washed with <n="84"/>3 x 20 ml of cold dichloromethane, and dried in vacuum. Yield 16.1 g (66%) of yellow crystalline product.Anal. calc. for C9H6Br4Zr: C, 20.59; H, 1.15. Found: C, 20.68; H, 1.20.1H NMR (CDCl3): δ 7.75 (dd, 2H, J = 6.5 Hz, J = 3.0 Hz, 5,6-H), 7.43 (dd, J = 6.5 Hz, J = 3.0 Hz, 2H, 4,7-H), 7.13 (s, 2H, 1,3-H).
66% To a solution of 9.49 g (48.7 mmol) of 2-bromo-lH-indene in 490 ml of ether, 12.3 g (46.3 mmol) of Zr(NMe2)4 was added. The reaction mixture was stirred for 12 h and then evaporated to dryness. The residue was dissolved in 500 ml of toluene, and 23.1 g (151 mmol) of bromotrimethylsilane was added. The mixture was stirred for 24 h at room temperature, evaporated to a volume equal to ca. 250 ml, and filtered through a glass frit (G4). Crystals that precipitated at a temperature of 3O0C from the filtrate were separated, washed with 3 x 20 ml of cold dichloromethane, and dried in vacuum. Yield 16.1 g (66%) of yellow crystalline product.Anal. calc. for C9H6Br4Zr: C, 20.59; H, 1.15. Found: C, 20.68; H, 1.20.1H NMR (CDCl3): δ 7.75 (dd, 2H, J = 6.5 Hz, J = 3.0 Hz, 5,6-H), 7.43 (dd, J = 6.5 Hz, J = 3.0 Hz, 2H, 4,7-H), 7.13 (s, 2H, 1,3-H).
  • 30
  • [ 10485-09-3 ]
  • [ 1301604-87-4 ]
  • 31
  • [ 10485-09-3 ]
  • [ 1123-56-4 ]
  • [ 1335329-00-4 ]
YieldReaction ConditionsOperation in experiment
40% (Comparative Example 3) 1.2 ml of a tetrahydrofuran solution of 0.25 g of magnesium was cooled to 0C, and 5.0 ml of a tetrahydrofuran solution of 1.0 g of <strong>[10485-09-3]2-bromoindene</strong> was slowly dropped thereto.After the dropping, the mixture was stirred at the same temperature for 1 hour, and 0.57 g of 2,6- dimethylbenzaldehyde was added thereto, and stirred for 12 hours while the temperature was being raised to 25C.After the confirmation of the degree of reaction progress by TLC, the reaction was terminated with an ammonium chloride aqueous solution, and an organic phase was extracted with ethyl acetate.[0132] After the obtained organic phase was dried with anhydrous magnesium sulfate, the organic phase was concentrated and purified by column chromatography. Then, 5 g of manganese dioxide was added to 30 ml of a chloroform solution of the obtained intermediate compound, and the mixture was stirred at 25 C for 12 hours. After the confirmation of the degree of reaction progress by TLC, the manganese dioxide was filtered, and 0.42 g (yield: 40%) of Comparative Product 3 shown below was obtained by recrystallization. Thestructure of Comparative Product 3 was confirmed by 1HNMR. 1H-NMR (CDC13; TMS) : δ 2.21 (s, 6H) , 3.85 (s, 2H) , 7.07 (d, 2H) , 7.20-7.26 (m, 2H) , 7.33-7.41 (m, 2H) , 7.47 (d, 1H) , 7.58 (d, 1H)
  • 32
  • [ 54221-96-4 ]
  • [ 2083-91-2 ]
  • [ 10485-09-3 ]
  • 1-(1H-inden-2-yl)-1-(6-methoxypyridin-2-yl)-N,N-dimethylmethanamine [ No CAS ]
 

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