(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid → HCID 86687515, compound

HRID 1473467Notes

Reaction equation

HRID 1473467 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]([C:31]#[N: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>>[C:31]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)(=[O:13])=[O:14])[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)#[N:32]

Participants

3

Reactant 2

HCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 86687516HCID 86687516, compound

Product 1

HCID 86687515HCID 86687515, compound

Procedure

The title compound was prepared in an analogous manner to that of Example 228, except that 1-chloro-4-cyano-N-(4-methoxybenzyl)-N-(pyrimidin-4-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 50 to 100% EtOAc:Heptane) to afford 4-cyano-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=9.30 (s, 1H), 8.68-8.51 (m, 2H), 8.14 (d, J=9.6 Hz, 1H), 7.91 (d, J=8.7 Hz, 1H), 7.67-7.60 (m, 1H), 7.59-7.49 (m, 2H), 3.76 (s, 3H). m/z (ESI) 486.2 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that of Example 228
  2. customThe final compound was purified via column chromatography (12 g silica gel column, gradient elution 50 to 100% EtOAc:Heptane)

Sources & evidence

ORD record
ord-2df2f50cb00847da8f4602c2ee39b9b6
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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