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Chemical Structure| 52092-47-4 Chemical Structure| 52092-47-4
Chemical Structure| 52092-47-4

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CAS No.: 52092-47-4

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Product Details of [ 52092-47-4 ]

CAS No. :52092-47-4
Formula : C5H3ClN2O2
M.W : 158.54
SMILES Code : C1=C(C=CC(=N1)[N+]([O-])=O)Cl
MDL No. :MFCD03092916
InChI Key :YUBHMOQVHOODEI-UHFFFAOYSA-N
Pubchem ID :259806

Safety of [ 52092-47-4 ]

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

Calculated chemistry of [ 52092-47-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 38.07
TPSA ?

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

58.71 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.14
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

1.6
Log Po/w (WLOGP)?

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

1.64
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.

0.68
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

-0.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.0

Water Solubility

Log S (ESOL):?

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

-2.21
Solubility 0.98 mg/ml ; 0.00618 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.

-2.44
Solubility 0.57 mg/ml ; 0.00359 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

-2.01
Solubility 1.55 mg/ml ; 0.00979 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

 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

 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.

-6.13 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

 1.0
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

2.0 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)

 1.99

Application In Synthesis of [ 52092-47-4 ]

* 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 [ 52092-47-4 ]

[ 52092-47-4 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 1072-98-6 ]
  • [ 52092-47-4 ]
YieldReaction ConditionsOperation in experiment
71% With sulfuric acid; dihydrogen peroxide; at 20℃; for 48h; [01066] After conc. sulfuric acid (50 ml) was cooled with ice, 30percent aqueous solution of hydrogen peroxide (25 ml) was dropped thereto stirring, and then conc. sulfuric acid (50 ml) solution of 2-amino-5-chloropyridine (5.0 g, 38.9 mmol) was dropped thereto further and stirred for 48 hours at the room temperature. The reaction mixture was added into ice and filtered. The residue was recrystallized with ethanol to obtain 4.38 g (yield 71percent) of 5-chloro-2-nitoropyriine as a colorless powdery crystal.
With sulfuric acid; dihydrogen peroxide; at 0 - 20℃; for 20h; Step A: 5-Chloro-2-nitropyridine To concentrated H2SO4 (50 mL) was added 30 percent H202 (25 mL) at 0 °C and a solution of 5- chloropyridin-2-amine (5.0 g, 39 mmol) in concentrated H2S04 (20 mL) was added at 0 °C. The mixture was stirred for 20 hours at room temperature. The mixture was poured into ice water under vigorous stirring and the resulting solid was filtered. The solid was recrystallized from ethanol to give 5-chloro-2-nitropyridine. 1H-NMR (400MHz, CDC13) delta 8.58 (d, J=2.8 Hz, 1H), 8.23 (d, J=8.8 Hz, 1H), 8.00 (dd, J=2.8 Hz, 8.8Hz, 1H). LC/MS m/z 159 (M+l)+.
With sulfuric acid; dihydrogen peroxide; In water; at 20℃; for 20h; Step A: 5-chloro-2-nitropyridine: To concentrated H2SO4 (50 mL) was added 30 percent H2O2 (25 mL) at 0 °C and a solution of 5-chloropyridin-2-amine (5.0 g, 39 mmol) in concentrated H2SO4 (20 mL) at 0 °C. The mixture was stirred for 20 hours at room temperature. The mixture was poured into ice water under vigorous stirring and the resulting solid was filtered. The solid was recrystallized from ethanol to give 5-chloro-2-nitropyridine.
With sulfuric acid; dihydrogen peroxide; In water; at 0 - 20℃; for 20h; Step A: 5-chloro-2-nitropyridine: To concentrated H2SO4 (50 mL) was added 30 percent H202 (25 mL) at 0 °C and a solution of 5-chloropyridin-2-amine (5.0 g, 39 mmol) in concentrated H2S04 (20 mL) at 0 °C. The mixture was stirred for 20 hours at room temperature. The mixture was poured into ice water under vigorous stirring and the resulting solid was filtered. The solid was recrystallized from ethanol to give 5-chloro-2-nitropyridine.
With sulfuric acid; dihydrogen peroxide; at 0 - 20℃; for 20h; [0217] To concentrated H2SO4 (50 mL) was added 30 percent H2O2 (25 mL) at 0 °C and a solution of 5-chloropyridin-2-amine (5.0 g, 39 mmol) in concentrated H2SO4 (20 mL) was added at 0 °C. The mixture was stirred for 20 hours at roomtemperature. The mixture was poured into ice water under vigorous stirring and the resulting solid was filtered. The solidwas recrystallized from ethanol to give 5-chloro-2-nitropyridine. 1H-NMR (400MHz, CDCl3) delta 8.58 (d, J=2.8 Hz, 1H),8.23 (d, J=8.8 Hz, 1H), 8.00 (dd, J=2.8 Hz, 8.8Hz, 1H). LC/MS m/z 159 (M+1)+.

  • 2
  • [ 52092-47-4 ]
  • [ 141-52-6 ]
  • [ 22109-30-4 ]
  • 3
  • [ 52092-47-4 ]
  • [ 1072-98-6 ]
  • 6
  • [ 99848-04-1 ]
  • [ 52092-47-4 ]
  • 8
  • [ 52092-47-4 ]
  • [ 3167-49-5 ]
  • 10
  • [ 15128-91-3 ]
  • [ 52092-47-4 ]
  • 11
  • [ 101079-67-8 ]
  • [ 52092-47-4 ]
  • 12
  • [ 52092-47-4 ]
  • [ 5188-07-8 ]
  • [ 35196-09-9 ]
YieldReaction ConditionsOperation in experiment
45% In methanol; at 0 - 20℃; for 13h; [01067] A methanol (40 mml) solution of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (2.0 g, 12.6 mmol) was added dropwise to a methanol (20 ml) solution of sodium thiomethoxide (1.02 g, 13.9 mmol) while being cooled with ice, and after the mixture was stirred for 13 hours while raising its temperature to the room temperature, water added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the resulting crude product was recrystalized with ethyl acetate-hexane to obtain 972 mg (yield 45percent) of 5-methylthio-2-nitropyridine.
In ethanol; EXAMPLE 61: 5-(METHYLSULFONYL)-3-NITRO-2-AMINOPYRIDINE <strong>[52092-47-4]5-Chloro-2-nitropyridine</strong> (8.0 grams) was added to a solution of 2.5 grams of sodium methanethiolate in 100 milliliters of ethanol at a temperature of 0°C. to which solution excess sodium methanethiolate was added portionwise. The resulting reaction mixture was then heated to reflux and refluxed for 15 hours with constant stirring. At the end of the 15 hours, the reaction mixture was filtered and allowed to concentrate to 75 milliliters. The reaction mixture was then permitted to cool and filtered again, yielding the desired 5-(methylthio)-2-nitropyridine; it was recrystallized from ethanol, m.p., 100.5-02.5°C.
In ethanol; EXAMPLE 61 5-(METHYLSULFONYL)-3-NITRO-2-AMINOPYRIDINE <strong>[52092-47-4]5-Chloro-2-nitropyridine</strong> (8.0 grams) was added to a solution of 2.5 grams of sodium methanethiolate in 100 milliliters of ethanol at a temperature of 0°C. to which solution excess sodium methanethiolate was added portionwise. The resulting reaction mixture was then heated to reflux and refluxed for 15 hours with constant stirring. At the end of the 15 hours, the reaction mixture was filtered and allowed to concentrate to 75 milliliters. The reaction mixture was then permitted to cool and filtered again, yielding the desired 5-(methylthio)-2-nitropyridine; it was recrystallized from ethanol, m.p., 100.5°-02.5°C.
In ethanol; EXAMPLE 61 5-(METHYLSULFONYL)-3-NITRO-2-AMINOPYRIDINE <strong>[52092-47-4]5-Chloro-2-nitropyridine</strong> (8.0 grams) was added to a solution of 2.5 grams of sodium methanethiolate in 100 milliliters of ethanol at a temperature of 0° C. to which solution excess sodium methanethiolate was added portionwise. The resulting reaction mixture was then heated to reflux and refluxed for 15 hours with constant stirring. At the end of the 15 hours, the reaction mixture was filtered and allowed to concentrate to 75 milliliters. The reaction mixture was then permitted to cool and filtered again, yielding the desired 5-(methylthio)-2-nitropyridine; it was recrystallized from ethanol, m.p., 100.5°-02.5° C.
270 g In methanol; water; at 0 - 20℃; The methanol solution (2000 mL) of methyl sodium sulfide (150 g) was added dropwise into the methanol solution (4000 mL) of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (300 g), and the reaction temperature was kept below 0° C. After completing the dropping, the reactant was heated to room temperature, and stirred overnight. The solvent of the reaction mixture was discarded and 5 liters of water was added into the residue, then extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, and dried with anhydrous sodium sulfate. The yellow and solid target compound (270 g) was obtained by filtration and concentration under reduced pressure. 1H-NMR (300 MHz, CDCl3) delta 2.61 (3H, s), 7.73 (1H, dd), 8.18 (1H, d), 8.40 (1H, d). LC-MS m/z: 171 [M++1].
In methanol; at 0 - 20℃; for 2h; Example 117a 5-(Methylthio)-2-nitropyridine 117a To a mixture of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (3 g, 18 mmol) in MeOH (20 mL), sodium methanethiolate (1.4 g, 20 mmol) was added at 0 °C and the mixture stirred at 20 °C for 2 hours. The resulting suspension was filtered and washed with water, and dried in vacuum to afford crude 117a as a yellow solid (2 g, 66percent) without purification for next step. MS: [M+H]+ 171.

YieldReaction ConditionsOperation in experiment
63% Example 297A 5-chloro-2-nitropyridine To cold (0° C.) concentrated sulfuric acid (80 mL) was added 30percent hydrogen peroxide (40 mL). To this solution was added 2-amino-5-chloropyridine (4.00 g, 31.11 mmol). The solution became lime colored within 30 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 20 hours. The reaction mixture was then poured into ice water and a white precipitate formed. This solid was filtered and dried in vacuo to afford 5-chloro-2-nitropyridine (3.10 g, 63percent yield). MS (DCI/NH3) m/e 129 (M+H for aniline)+; 1H NMR (DMSO-d6, 300 MHz) delta8.78 (m, 1H), 8.37 (m, 2H).
  • 14
  • [ 52092-47-4 ]
  • [ 14704-41-7 ]
  • 5-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-2-nitropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In N-methyl-acetamide; hexane; ethyl acetate; Example 297B 5-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-2-nitropyridine To a cold slurry (0° C.) of sodium hydride (95percent, 439 mg, 18.30 mmol) in dimethylformamide 3.0 mL) was added 3,5-bis(trifluoromethyl)pyrazole (2.50 g, 12.30 mmol). The resulting suspension was stirred for 30 minutes. A solution of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (1.90 g, 12.00 mmol) was added. The resulting mixture was heated at reflux for 24 hours, then cooled to room temperature. The mixture was poured into saturated sodium chloride solution (100 mL). The aqueous mixture was extracted with ethyl acetate (3*100 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using 20percent ethyl acetate/hexane to afford a yellow oil (1.17 g, 30percent yield). MS (DCI/NH3) nme 297 (M+1 for aniline)+; 1H NMR (DMSO-d6, 300 MHz) delta9.38 (d, 1H), 8.88 (dd, 1H), 8.21 (d, 1H), 8.02 (s, 1H).
  • 15
  • [ 52092-47-4 ]
  • [ 106-54-7 ]
  • [ 77012-86-3 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide; In N,N-dimethyl-formamide; EXAMPLE 15 2-NITRO-5-(4-CHLOROPHENYLTHIO)PYRIDINE <strong>[52092-47-4]2-Nitro-5-chloropyridine</strong> (9.5 grams), 4-chlorothiophenol (8.7 grams), and lithium hydroxide (4 grams) were mixed in 100 ml. of DMF and the reaction mixture was stirred overnight (about 18 hours) at room temperature. The reaction mixture was then poured into water and the product separated by filtration and crystallized from ethanol-hexanes, yield, 10.0 grams, m.p., 96°-98° C. Calc. for C11 H7 ClN2 O2 S: C, 49.54; H, 2.65; N, 10.50. Found: C, 49.31; H, 2.88; N, 10.38.
  • 16
  • [ 1072-98-6 ]
  • concentrated H2 SO4 [ No CAS ]
  • [ 7722-84-1 ]
  • [ 52092-47-4 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; toluene; EXAMPLE 14 2-NITRO-5-CHLOROPYRIDINE 2-Amino-5-chloropyridine (50 grams) was added portionwise to a solution of 300 ml. of concentrated H2 SO4 and 150 ml. of 30percent H2 O2, maintained at a temperature of 0°-5° C., over a period of 5.0 hours. The reaction mixture was then allowed to rise to room temperature and stirred at room temperature for 24 hours. The reaction mixture was then poured over ice, and the product residue separated by filtration and air dried. Crystallization from ethyl acetae-ethanol gave only the azo compound. The remainder of the product residue was passed over a column of silica gel with a mixture of 1:1 toluene:ethyl acetate. The desired product was isolated and its identity confirmed by NMR.
  • 17
  • [ 52092-47-4 ]
  • [ 953771-42-1 ]
  • [ 1086110-88-4 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 85℃; for 16h; To a reaction mixture of (S)-2-(l-cyclohexylethylamino)benzo[d]thiazol-6-ol (25 mg, 0.095 mmol; see Example 2 above) and cesium carbonate (78 mg, 0.239 mmol) in 0.6 mL of NMP was added <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (22.7 mg, 0.143 mmol). The reaction <n="88"/>mixture was stirred at 85 °C for 16 hours. The crude reaction mixture was filtered, purified by preparative HPLC and lyophilized to give the title compound as its TFA salt (13 mg). ES/MS m/z 398.9 (MH+), Rt = 2.86 min.
  • 18
  • [ 52092-47-4 ]
  • [ 1195781-15-7 ]
  • [ 1195781-16-8 ]
YieldReaction ConditionsOperation in experiment
83% With caesium carbonate; In dimethyl sulfoxide; at 20℃; for 3h; To a solution of benzyl (3-fluoro-4- hydroxyphenyl) carbamate (80 g, 252 mmol) in dimethyl sulfoxide (600 mL) were added cesium carbonate (123 g, 378 mmol) and 5- chloro-2-nitropyridine (40 g, 252 mmol), and the mixture was <n="138"/>stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate (1000 mL) and water (1000 mL) were added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (=3/1) and collected by filtration to give the title compound (79.8 g, 83percent) . 1H-NMR (CDCl3, 300MHz) delta 5.23 (2H, S), 6.82 (IH, s) , 7.05 -7.19 (2H, m) , 7.31 - 7.44 (6H, m) , 7.59 (IH, dd, J = 12.3, 2.4 Hz), 8.24 (IH, d, J = 9.0 Hz), 8.32 (IH, d, J = 2.7 Hz) .
  • 19
  • [ 52092-47-4 ]
  • [ 1195781-24-8 ]
  • [ 1195781-25-9 ]
YieldReaction ConditionsOperation in experiment
77% With caesium carbonate; In dimethyl sulfoxide; at 20℃; for 6h; To a solution of benzyl (2-fluoro-4- hydroxyphenyl) carbamate (79 g, 303 mmol) in dimethyl sulfoxide (480 mL) were added cesium carbonate (123 g, 378 mmol) and 5- chloro-2-nitropyridine (40 g, 252 mmol) , and the mixture was <n="143"/>stirred at room temperature for 6 hr. Water (1000 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (=3/1) and collected by filtration to give the title compound (74 g, 77percent) .1H-NMR (DMSOd6, 300MHz) delta 5.17 (2H, s) , 7.05 - 7.12 (IH, m) , 7.27 - 7.46 (6H, m) , 7.66 - 7.78 (2H, m) , 8.34 (IH, d, J = 8.6 Hz), 8.46 (IH, d, J = 2.9 Hz), 9.57 (IH, s)
  • 20
  • [ 52092-47-4 ]
  • [ 392-04-1 ]
  • methyl 4-fluoro-2-((6-nitropyridin-3-yl)oxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 1h; A mixture of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (2.5 g, 15.75 mmol), methyl 4-fluoro-2-hydroxybenzoate (2.44 g, 14.38 mmol), K 2CO 3 (3.96 g, 28.65 mmol) in DMSO (30 mL) was stirred at 110 C for 1 hour. TLC showed the reactant was consumed completely. The reaction mixture was cooled to room temperature and was poured into water and was then extracted with EA (40 mL 3). The combined organic layers were washed with brine (50 mL 2), dried over Na 2SO 4, filtered and concentrated to give a residue. The residue was purified by column chromatography on silica gel (eluent: PE/EA = 50/1 to 1/1) to obtain methyl 4-fluoro-2- ((6-nitropyridin-3-yl) oxy) benzoate (1.3 g). MS (ESI, m/e) [M+1] + 293.5.
  • 21
  • [ 52092-47-4 ]
  • (2S,3'S)-2-methyl[1,3']bipyrrolidinyl dihydrochloride [ No CAS ]
  • [ 1350410-92-2 ]
YieldReaction ConditionsOperation in experiment
17% With potassium carbonate; In acetonitrile; at 45 - 65℃; for 2h; Intermediate (xxiv)(2S,3'S)-2-Methyl-1 '-(6-nitro-pyridin-3-yl)-[1 ,3']bipyrrolidinyl To a solution of (2S,3'S)-2-methyl-[1 ,3']bipyrrolidinyl dihydrochloride (0.53 g, 2.35 mmol,) in acetonitrile (25 mL) was added <strong>[52092-47-4]5-chloro-2-nitro-pyridine</strong> (0.561 g, 3.53 mmol,) and powdered potassium carbonate (1 .3 g, 9.4 mmol). The reaction mixture was then heated to 65°C for 4.0 hr, then at 45°C for 16 hr. The reaction mixture was then allowed to cool to room temperature and filtered through a 10 g Varian Bond Elut SCX (stong cation-exchange) cartridge eluting with 50 mL of (1 :1 ) methanol in dichloromethane, 25 mL of methanol, followed by 7N ammonia in methanol (50 mL).The filtrate was concentrated under vacuum to obtain a compound which was purified again by column chromatography on silica gel eluting with methanol in dichloromethane (0-10percent) to afford 0.1 1 g (17percent) of the title compound..LC/MS: LC RT = 0.899 min. MS (ESI) m/z = 277 (M+H+)
17% With potassium carbonate; In acetonitrile; at 45 - 65℃; for 20h; Intermediate (xvi)Meth l-1 '-(6-nitro-pyridin-3-yl)-[1 ,3']bipyrrolidinylTo a solution of (2S,3'S)-2-methyl-[1 ,3']bipyrrolidinyl dihydrochloride (0.530 g, 2.35 mnnol,) in acetonitrile (25 mL) was added <strong>[52092-47-4]5-chloro-2-nitro-pyridine</strong> (0.561 g, 3.53 mnnol,) and powdered potassium carbonate (1 .30 g, 9.40 mmol). The reaction mixture was then heated to 65°C for 4.0 hr, then at 45°C for 16 hr. The reaction mixture was then allowed to cool to room temperature and filtered through a 10.0 g Varian Bond Elut SCX (stong cation-exchange) cartridge eluting with 50 mL of (1 :1 ) methanol in dichloromethane, 25 mL of methanol, followed by 7N ammonia in methanol (50 mL). The filtrate was concentrated under vacuum to obtain a compound which was purified again by column chromatography on silica gel eluting with methanol in dichloromethane (0-10percent) to afford 0.1 10 g (17percent) of the title compound.LC/MS: LC RT = 0.899 min. MS (ESI) m/z =277 (M+H+)
  • 22
  • [ 110-85-0 ]
  • [ 52092-47-4 ]
  • [ 1221726-34-6 ]
YieldReaction ConditionsOperation in experiment
82.3% In butan-1-ol; at 95℃; for 24h;Inert atmosphere; A nitrogen-flushed, suitably equipped 22 L 4-neck round bottom flask is charged with 1392 g (8.78 mol, 1.0 eq.) of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (A2d), 1512 g (17.56 mol, 2.0 eq.) of piperazine (A2c) and 11,340 g (14,000 mL) of n-butanol.The resulting suspension is stirred and heated to 95° C.This temperature is maintained for at least 24 h or until the remaining starting material, A2d, is ?2percent (area normalization) as determined by HPLC analysis.The resulting slurry is cooled to 25° C. over 1 h.The solids are filtered through a polypropylene filter pad.The filter cake is washed twice with a total of 2267 g (2*1300 mL) of isopropyl acetate.The solids are dried at 60° C. for 16 h, to afford 1769 g (82.3percent, uncorrected) of A2b as a yellow, crystalline solid, mp>230° C. (dec.).
  • 23
  • [ 52092-47-4 ]
  • [ 603-35-0 ]
  • C23H18N3O2P [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium azide; In dimethyl sulfoxide; at 120℃; General procedure: A round bottom flask equipped with reflux condenser and magnetic stirring bar was charged with substituted heteroaryl chloride (5 mmol), sodium azide (10 mmol), triphenylphosphine (10 mmol) and DMSO (40 ml). The reaction mixture was stirred at 120 °C. Reaction progress was monitored by TLC. In 3-5 hours starting material was disappeared and new product was confirmed by TLC. 1N HCl (8 mL) was added to the reaction mixture and continued to stir at 120 °C for additional 1-2 hour. Reaction mixture was cooled to room temperature and diluted with 1N HCl (8 mL). The resulting mixture was poured into distilled water (100 mL) and aqueous layer was washed with EtOAc (2 X 50 mL) to remove triphenylphosphine oxide. Aqueous layer was slowly neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc (2 X 50 mL). The combined organic layers were washed with water (40 mL), brine(40 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford substituted heteroaryl amine with high purity without column purification ?(purity was achieved in some products by washing solid compound with n-Pantane).
  • 24
  • [ 52092-47-4 ]
  • [ 1426259-92-8 ]
  • 25
  • [ 52092-47-4 ]
  • [ 866620-36-2 ]
  • 26
  • [ 4318-42-7 ]
  • [ 52092-47-4 ]
  • [ 943758-04-1 ]
  • 27
  • [ 52092-47-4 ]
  • [ 1374129-88-0 ]
  • 28
  • [ 52092-47-4 ]
  • [ 1374128-87-6 ]
  • 29
  • [ 52092-47-4 ]
  • [ 1374128-86-5 ]
 

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