(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid → HCID 86687508, compound

HRID 1473462Notes

Reaction equation

HRID 1473462 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]([OH:32])=[CH:4][N:3]=1.[CH3:33][O:34][C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][C:36]=1B(O)O>>[OH: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:14])=[O:13])[CH:7]=2)[C:2]([C:36]2[CH:37]=[CH:38][C:39]([C:41]([F:44])([F:43])[F:42])=[CH:40][C:35]=2[O:34][CH3:33])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 86687509HCID 86687509, compound

Product 1

HCID 86687508HCID 86687508, compound

Procedure

Example 232 was synthesized in a similar manner to Example 228, except that 1-chloro-N-(2,4-dimethoxybenzyl)-4-hydroxy-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 5% MeOH:DCM) to afford 4-hydroxy-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.89 (s, 1H), 11.03 (s, 1H), 8.64 (d, J=1.4 Hz, 1H), 8.24 (s, 1H), 7.84 (dd, J=1.8, 8.9 Hz, 1H), 7.60 (d, J=8.9 Hz, 1H), 7.55-7.49 (m, 1H), 7.48-7.42 (m, 2H), 7.28 (d, J=4.6 Hz, 1H), 6.86 (d, J=4.5 Hz, 1H), 3.73 (s, 3H). m/z (ESI) 482.2 (M+H)+.

Workup

  1. customThe final compound was purified via column chromatography (12 g silica gel column, gradient elution 0 to 5% MeOH:DCM)

Sources & evidence

ORD record
ord-388d1ce711244ac8bfeedf374c1d65da
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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