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

HRID 2264750Notes

Reaction equation

HRID 2264750 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][C:19]=3[F:24])[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:25][C:26]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>>[F:25][C:26]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][C:19]=3[F:24])[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 595962811-(3-Bromophenyl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amine

Product 1

HCID 248746961-(2'-Fluoro-3'-methoxybiphenyl-3-yl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amineYield 69%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(3-fluoropyridin-4-yl)-1H-isoindol-3-amine (Scheme #12, I) as described in Example 67 (Scheme #10, D) in 69% yield using 2-fluoro-3-methoxyphenylboronic acid. 1H NMR (DMSO-d6) δ 8.26 (d, J=2.78 Hz, 1 H), 8.14 (d, J=5.05 Hz, 1 H), 7.67-7.61 (m, 1 H), 7.55-7.50 (m, 1 H), 7.34-7.28 (m, 2 H), 7.21-7.10 (m, 4 H), 7.07-6.92 (m, 3 H), 6.77 (br s, 2 H), 6.74-6.68 (m, 1 H), 3.65 (s, 3 H); MS (ESI) m/z 428 [M+1]+.

Sources & evidence

ORD record
ord-544af8d1aab6436f86fa673d3bc17303
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

Loading…