(Pyrimidin-5-yl)boronic acid → 4-Fluoro-1-(6-methoxy-5-(trifluoromethyl)pyridin-3-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

HRID 1662268Notes

Reaction equation

HRID 1662268 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:20]=[N:21][C:22]([O:29][CH3:30])=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[N:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[N:33][CH:32]=1>>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:19]1[CH:20]=[N:21][C:22]([O:29][CH3:30])=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:35]2[CH:36]=[N:31][CH:32]=[N:33][CH:34]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 585794811-(3-Bromophenyl)-4-fluoro-1-(6-methoxy-5-(trifluoromethyl)pyridin-3-yl)-1H-isoindol-3-amine

Product 1

HCID 462030734-Fluoro-1-(6-methoxy-5-(trifluoromethyl)pyridin-3-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amineYield 79%

Procedure

The title compound was synthesized as described for Example 1 in 79% yield, starting from 1-(3-bromophenyl)-4-fluoro-1-(6-methoxy-5-(trifluoromethyl)pyridin-3-yl)-1H-isoindol-3-amine (680 mg, 1.42 mmol), pyrimidin-5-ylboronic acid (211 mg, 1.70 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.18 (s, 1 H) 9.05 (s, 2 H) 8.41 (d, 1 H) 7.91 (d, 1 H) 7.87 (d, 1 H) 7.66-7.72 (m, 2 H) 7.56 (td, 1 H) 7.44-7.52 (m, 2 H) 7.28 (dd, 1 H) 6.72 (br. s., 2 H) 3.94 (s, 3 H); MS (ES+) m/z 480 [M+1]+.

Sources & evidence

ORD record
ord-656bbcd55e86496b84b50cb7ba13e6fe
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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