2-Fluoro-3-methoxyphenylboronic acid → 1-(2',6-Difluoro-3'-methoxybiphenyl-3-yl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amine

HRID 2264751Notes

Reaction equation

HRID 2264751 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][C:20]=3[F:25])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:26][C:27]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>>[F:26][C:27]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:28]=1[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([C:9]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][C:20]=3[F:25])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:3]=1

Participants

3

Reactant 2

HCID 49857442-Fluoro-3-methoxyphenylboronic acidHCID 59596245HCID 59596245, compound

Product 1

HCID 248746971-(2',6-Difluoro-3'-methoxybiphenyl-3-yl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amineYield 25%

Procedure

The title compound was synthesized from 1-(3-bromo-4-fluorophenyl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amine (Example 70) as described in Example 67 Scheme #10, D in 25% yield using 2-fluoro-3-methoxyphenyl boronic acid. 1H NMR (DMSO-d6) δ 8.39 (d, J=3.03 Hz, 1 H), 8.26 (d, J=5.05 Hz, 1 H), 7.83-7.73 (m, 1 H), 7.71-7.64 (m, 1H), 7.48-7.39 (m, 2 H), 7.29-7.11 (m, 6 H), 6.92 (br s, 2 H), 6.81-6.73 (m, 1 H), 3.79 (s, 3 H); MS (ESI) m/z 446 [M+1]+.

Sources & evidence

ORD record
ord-dbb988cb2f64413c933dc6a291e884ec
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

Loading…