2-Cyano-4-(trifluoromethyl)phenylboronic acid → 1-(2-cyano-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=3[O:30][CH3:31])[C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:32]([C:34]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:35]=1B(O)O)#[N:33]>>[C:32]([C:34]1[CH:39]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:37]=[CH:36][C:35]=1[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=3[O:30][CH3:31])[C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1)#[N:33]Participants
3
Procedure
The titled compound was prepared in an analogous manner to that of INTERMEDIATE DD, except that 1-chloro-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (Intermediate OOO) and (2-cyano-4-(trifluoromethyl)phenyl)boronic acid were used as the coupling partners. The material was purified via silica gel column chromatography (12 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 1-(2-cyano-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a light yellow solid. m/z (ESI) 629.3 (M+H)+.
Workup
- customThe titled compound was prepared in an analogous manner to that of INTERMEDIATE DD
- customThe material was purified via silica gel column chromatography (12 g, gradient elution 0 to 50% EtOAc:Heptane)
Sources & evidence
- ORD record
- ord-088884afc2d64ff186d5beba53a99494
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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