2-Fluoro-3-methoxyphenylboronic acid → 1-(2'-Fluoro-3'-methoxybiphenyl-3-yl)-1-pyridin-4-yl-1H-isoindol-3-amine

HRID 2264752Notes

Reaction equation

HRID 2264752 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:24][C:25]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>>[F:24][C:25]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:3]=1

Participants

3

Reactant 2

HCID 49857442-Fluoro-3-methoxyphenylboronic acidHCID 595962471-(3-Bromophenyl)-1-pyridin-4-yl-1H-isoindol-3-amine

Product 1

HCID 248747371-(2'-Fluoro-3'-methoxybiphenyl-3-yl)-1-pyridin-4-yl-1H-isoindol-3-amineYield 50%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-pyridin-4-yl-1H-isoindol-3-amine (Scheme #9, C) as described in Example 67 Scheme #10, D in 50% yield using 2-fluoro-3-methoxyphenyl boronic acid. 1H NMR (DMSO-d6) δ 8.42-8.32 (m, 2 H), 7.78-7.67 (m, 2 H), 7.44-7.34 (m, 3 H), 7.34-7.20 (m, 5 H), 7.15-7.02 (m, 2 H), 6.92-6.74 (m, 3 H), 3.78 (s, 3 H); MS (ESI) m/z 410 [M+1]+.

Sources & evidence

ORD record
ord-5b9c635a36014eefa6bb876093957e29
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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