N-(4-ethynylphenyl)-4-fluorobenzamide → (S)-5-({4-[(4-fluorobenzoyl)amino]phenyl}ethynyl)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 391541Notes

Reaction equation

HRID 391541 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[CH:2].Br[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:37]=1)[C:25]([N:27]=[S:28]([CH3:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:20]3[CH:21]=[N:22][CH:23]=[C:24]([CH:37]=3)[C:25]([N:27]=[S@@:28]([CH3:36])(=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[CH:8][CH:7]=2)=[O:18])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 4271639N-(4-ethynylphenyl)-4-fluorobenzamideHCID 576578195-bromo-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

Product 1

HCID 24952783(S)-5-({4-[(4-fluorobenzoyl)amino]phenyl}ethynyl)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideYield 72.2%

Procedure

In a manner similar to that described in Example 449, N-(4-ethynyl-phenyl)-4-fluoro-benzamide (0.106 g, 0.443 mmol) and 5-bromo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide (100 mg, 0.295 mmol) were reacted to give the title compound as a solid (106 mg, 72%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-16a7337e86fc448fbffa144079fcadb2
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

Loading…