4-Cyano-2-methoxyphenylboronic acid → 1-(4-cyano-2-methoxyphenyl)-4-fluoro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15](CC3C=CC(OC)=CC=3)[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([F:31])=[CH:4][N:3]=1.[C:32]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[C:36]([O:43][CH3:44])[CH:35]=1)#[N:33]>>[C:32]([C:34]1[CH:39]=[CH:38][C:37]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]4[CH:21]=[CH:20][N:19]=[CH:18][N:17]=4)(=[O:13])=[O:14])=[CH:9][CH:10]=3)[C:5]([F:31])=[CH:4][N:3]=2)=[C:36]([O:43][CH3:44])[CH:35]=1)#[N:33]Participants
3
Procedure
Example 218 was synthesized in a similar manner to Example 212, except that 1-chloro-4-fluoro-N-(4-methoxybenzyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (Intermediate QQQ) and (4-cyano-2-methoxyphenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (12 g silica gel column, gradient elution 25 to 100% EtOAc:Heptane) to afford 1-(4-cyano-2-methoxyphenyl)-4-fluoro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.74 (s, 1H), 8.59 (d, J=15.7 Hz, 2H), 8.37-8.14 (m, 1H), 8.05 (d, J=7.4 Hz, 1H), 7.75 (d, J=1.3 Hz, 2H), 7.66-7.60 (m, 1H), 7.57-7.50 (m, 1H), 3.72 (s, 3H). m/z (ESI) 436.2 (M+H)+.
Workup
- customThe final compound was purified via column chromatography (12 g silica gel column, gradient elution 25 to 100% EtOAc:Heptane)
Sources & evidence
- ORD record
- ord-d2a3bea956a84ce68cd8bd30f47c8310
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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