Potassium Carbonate → 6-fluoro-2-(3-phenylpropylthio)-N-(thiophen-2-ylmethyl)pyridine-3-carboxylic acid amide

HRID 1925560Notes

Reaction equation

HRID 1925560 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]1([CH2:13][CH2:14][CH2:15][SH:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.F[C:18]1[N:32]=[C:31]([F:33])[CH:30]=[CH:29][C:19]=1[C:20]([NH:22][CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=[O:21].CCCCCC.CC(=O)OCC>CN(C=O)C>[F:33][C:31]1[N:32]=[C:18]([S:16][CH2:15][CH2:14][CH2:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:19]([C:20]([NH:22][CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[O:21])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 905963-Phenylpropane-1-thiolHCID 21226206Ethyl acetate hexaneHCID 671345172,6-difluoro-N-(thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 594873026-fluoro-2-(3-phenylpropylthio)-N-(thiophen-2-ylmethyl)pyridine-3-carboxylic acid amideYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

919 mg (6.0 mmol) of K2CO3 and 305 mg (2.0 mmol) of 3-phenylpropane-1-thiol were added to a solution of 509 mg (2.0 mmol) of 2,6-difluoro-N-(thiophen-2-ylmethyl)-nicotinamide in DMF (10 ml), and the mixture was stirred for 1 h at RT. Dilution with water and extraction with EA were then carried out. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 4:1) of the residue yielded 336 mg (0.9 mmol, 43%) of 6-fluoro-2-(3-phenylpropylthio)-N-(thiophen-2-ylmethyl)pyridine-3-carboxylic acid amide. MS: m/z 387.1 [M+H]+.

Workup

  1. extractionDilution with water and extraction with EA
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98d21fa88de348bfbf5f4e291463e37c
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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