(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid → HCID 86687512, compound

HRID 1473465Notes

Reaction equation

HRID 1473465 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.[CH3:34][O:35][C:36]1[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=1B(O)O>>[C:32]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:13])=[O:14])[CH:7]=2)[C:2]([C:37]2[CH:38]=[CH:39][C:40]([C:42]([F:45])([F:44])[F:43])=[CH:41][C:36]=2[O:35][CH3:34])=[N:3][CH:4]=1)#[N:33]

Participants

3

Reactant 2

HCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 86687513HCID 86687513, compound

Product 1

HCID 86687512HCID 86687512, compound

Procedure

Example 240 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 (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (12 g silica gel column, gradient elution 0 to 10% MeOH:EtOAc) to afford 4-cyano-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=13.07 (s, 1H), 9.29 (s, 1H), 8.52 (d, J=1.3 Hz, 1H), 8.06 (dd, J=1.8, 8.8 Hz, 1H), 7.92 (d, J=8.9 Hz, 1H), 7.65-7.60 (m, 1H), 7.56 (s, 1H), 7.55-7.52 (m, 1H), 7.32 (d, J=4.5 Hz, 1H), 6.93 (d, J=4.5 Hz, 1H), 3.76 (s, 3H). m/z (ESI) 491.1 (M+H)+.

Workup

  1. customThe final compound was purified via column chromatography (12 g silica gel column, gradient elution 0 to 10% MeOH:EtOAc)

Sources & evidence

ORD record
ord-c685a37d6a0e4480b8cae6f1536825b2
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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