2-Fluoro-3-methoxyphenylboronic acid → 1-(2'-Fluoro-3'-methoxybiphenyl-3-yl)-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amine

HRID 2264756Notes

Reaction equation

HRID 2264756 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:19]=[N:20][C:21]([O:24][CH3:25])=[N: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:5]=[CH:6][CH:7]=1.[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[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2([C:18]3[CH:23]=[N:22][C:21]([O:24][CH3:25])=[N: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:3]=1

Participants

3

Reactant 2

HCID 49857442-Fluoro-3-methoxyphenylboronic acidHCID 59596264HCID 59596264, compound

Product 1

HCID 248747411-(2'-Fluoro-3'-methoxybiphenyl-3-yl)-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amineYield 27%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amine (Example 106) as described in Example 67 Scheme #10, D in 27% yield using 2-fluoro-3-methoxyphenylboronic acid. 1H NMR (DMSO-d6) δ 8.55 (s, 2H), 7.96-7.79 (m, 2 H), 7.58-7.43 (m, 3 H), 7.43-7.34 (m, 3 H), 7.24-7.12 (m, 2 H), 7.08-6.83 (m, 3 H), 3.88 (s, 3 H), 3.86 (s, 3 H); MS (ESI) m/z 441 [M+1]+.

Sources & evidence

ORD record
ord-9f75b28af8b6454ea2562f41705c8c80
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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