(4-Fluoro-2-methoxyphenyl)boronic acid → 4-fluoro-1-(4-fluoro-2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-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=3OC)[C:16]3[S:20][N:19]=[CH:18][N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([F:32])=[CH:4][N:3]=1.[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[C:36]([O:43][CH3:44])[CH:35]=1>>[F:32][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([NH:15][C:16]3[S:20][N:19]=[CH:18][N:17]=3)(=[O:13])=[O:14])[CH:7]=2)[C:2]([C:37]2[CH:38]=[CH:39][C:34]([F:33])=[CH:35][C:36]=2[O:43][CH3:44])=[N:3][CH:4]=1Participants
Procedure
The title compound was prepared in an analogous manner to that of EXAMPLE 228, except that 1-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide and (4-fluoro-2-methoxyphenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM) to afford 4-fluoro-1-(4-fluoro-2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=8.72 (d, J=1.5 Hz, 1H), 8.49 (s, 2H), 8.00 (dd, J=1.7, 8.9 Hz, 1H), 7.86-7.78 (m, 1H), 7.38 (dd, J=6.9, 8.3 Hz, 1H), 7.16 (dd, J=2.3, 11.4 Hz, 1H), 6.97 (dt, J=2.3, 8.4 Hz, 1H), 3.67 (s, 3H). m/z (ESI) 435.2 (M+H)+.
Workup
- customThe title compound was prepared in an analogous manner to that of EXAMPLE 228
- customThe final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM)
Sources & evidence
- ORD record
- ord-920ca849ed4c4d5da175cc6d38cac3be
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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