Potassium Carbonate → 1-(2-(6-(4-fluoro-phenylsulfanyl)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13357

Reaction equation

HRID 13357 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23]1[C:28](F)=[CH:27][C:26]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=O)=[C:25]([N+:39]([O-])=O)[CH:24]=1)(=[O:17])[CH3:16].O.O.[Sn](Cl)Cl>C(=O)(O)[O-].[Na+].CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:28]2[C:23]([CH:19]3[CH2:20][CH2:21][CH2:22][N:18]3[C:15](=[O:17])[CH3:16])=[CH:24][C:25]3[NH:39][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:30][C:26]=3[CH:27]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 677894-FluorothiophenolHCID 23145313Pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide

Product 1

HCID 231455871-(2-(6-(4-fluoro-phenylsulfanyl)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

20 mg of 4-fluoro-benzenethiol and 30 mg of potassium carbonate were added in order to an N,N-dimethylformamide (1 ml) solution of 50 mg of pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide, and the reaction liquid was stirred at 100° C. for 2 hours. 30 mg of tin(II) chloride dihydrate was added to the reaction liquid, and the reaction liquid was stirred at 100° C. for 3 hours. After cooled, the reaction liquid was diluted with aqueous saturated sodium bicarbonate and extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

Workup

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at 100° C. for 3 hours
  4. temperatureAfter cooled
  5. customthe reaction liquid
  6. extractionextracted with chloroform
  7. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. customThe resulting residue was purified
  10. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-193abfcda9f243b19d8caf7097c67caa
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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