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

HRID 2044180Notes

Reaction equation

HRID 2044180 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-e723367aedbc4715b084a31a50ee66de
Source dataset
uspto-grants-2013_11
Patent number
US08586755B2

Reaction notes

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