3-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamide → 3-cyano-4-[2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethoxy)phenoxy]-N-1,3-thiazol-2-ylbenzenesulfonamide
Reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=2[OH:18])=[CH:5][CH:4]=[N:3]1.[C:19]([C:21]1[CH:22]=[C:23]([S:28]([NH:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1F)#[N:20]>>[C:19]([C:21]1[CH:22]=[C:23]([S:28]([NH:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[O:18][C:8]1[CH:9]=[CH:10][C:11]([O:13][C:14]([F:15])([F:16])[F:17])=[CH:12][C:7]=1[C:6]1[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=1)#[N:20]Participants
3
Procedure
2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethoxy)phenol (Preparation 533, 50.0 mg, 0.20 mmol) and 3-cyano-4-fluoro-N-(1,3-thiazol-2-yl)benzenesulfonamide (Preparation 46, 57 mg, 0.20 mmol) were used to prepare the title compound using Method F above. The product was purified by flash column chromatography (SiO2) eluting with dichloromethane:ethyl acetate (gradient 8:2 to 2:8, by volume) to afford the title compound, 98 mg, 97% yield.
Sources & evidence
- ORD record
- ord-3e05485e9dd945d2a6883cd5fcc45459
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541588B2
Reaction notes
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