(4-Chloro-2-methoxyphenyl)boronic acid → 1-(4-chloro-2-methoxyphenyl)-4-fluoro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

HRID 1473446Notes

Reaction equation

HRID 1473446 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.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[C:35]([O:42][CH3:43])[CH:34]=1>>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([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:35]([O:42][CH3:43])[CH:34]=1

Participants

3

Reactant 2

HCID 3858606(4-Chloro-2-methoxyphenyl)boronic acidHCID 866874911-chloro-4-fluoro-N-(4-methoxybenzyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

Product 1

HCID 866874921-(4-chloro-2-methoxyphenyl)-4-fluoro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

Procedure

Example 217 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-chloro-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-chloro-2-methoxyphenyl)-4-fluoro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.70 (s, 1H), 8.58 (d, J=10.4 Hz, 2H), 8.21 (s, 1H), 8.05 (d, J=9.1 Hz, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.40-7.30 (m, 2H), 7.19 (dd, J=2.0, 8.0 Hz, 1H), 7.10-6.80 (m, 1H), 3.67 (s, 3H). m/z (ESI) 445.2 (M+H)+.

Workup

  1. 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-b5053ca633f44caba1ae912bb649a7f8
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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