(4-Chloro-2-methoxyphenyl)boronic acid → HCID 86687514, compound

HRID 1473466Notes

Reaction equation

HRID 1473466 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:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:32]#[N:33])=[CH:4][N:3]=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[C:37]([O:44][CH3:45])[CH:36]=1>>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]4[S:17][CH:18]=[CH:19][N:20]=4)(=[O:13])=[O:14])=[CH:9][CH:10]=3)[C:5]([C:32]#[N:33])=[CH:4][N:3]=2)=[C:37]([O:44][CH3:45])[CH:36]=1

Participants

3

Reactant 2

HCID 3858606(4-Chloro-2-methoxyphenyl)boronic acidHCID 86687513HCID 86687513, compound

Product 1

HCID 86687514HCID 86687514, compound

Procedure

Example 241 was synthesized in a similar manner to Example 228, except that 1-chloro-4-cyano-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide 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-cyano-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=13.06 (s, 1H), 9.26 (s, 1H), 8.58-8.43 (m, 1H), 8.06 (dd, J=1.8, 8.9 Hz, 1H), 7.94 (dd, J=0.6, 8.9 Hz, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.37 (d, J=1.9 Hz, 1H), 7.32 (d, J=4.6 Hz, 1H), 7.24 (dd, J=1.9, 8.1 Hz, 1H), 6.92 (d, J=4.6 Hz, 1H), 3.69 (s, 3H). m/z (ESI) 457.2 (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-f3f81a2cc9cf457890a2ff02376edd66
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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