Trimethylsilylacetylene → 2,2,2-Trifluoro-N-{2-fluoro-5-[(trimethylsilyl)ethynyl]phenyl}acetamide
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]1[CH:7]=[C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:3]=[CH:4][C:5]=1[F:15])=[O:14]Participants
3
Procedure
N-(5-Bromo-2-fluorophenyl)-2,2,2-trifluoroacetamide (8.04 g, 28 mmol) and (trimethylsilyl)acetylene (6 mL, 42 mmol) were coupled according to the procedure of Example 56, Step B to give the desired product (6.66 g, 78%). 1H NMR (400 MHz, d6-DMSO) δ 11.32 (s, 1H), 7.62-7.60 (m, 1H), 7.47-7.44 (m, 1H), 7.39-7.33 (m, 1H), 0.21 (s, 9H) ppm.
Sources & evidence
- ORD record
- ord-07214f5635094efab7003dbfc09dae8a
- Source dataset