2-Fluoro-3-methoxyphenylboronic acid → 1-(2',6-Difluoro-3'-methoxybiphenyl-3-yl)-4-fluoro-1-(pyrimidin-5-yl)-1H-isoindol-3-amine

HRID 1662239Notes

Reaction equation

HRID 1662239 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:20]3[CH:21]=[N:22][CH:23]=[N:24][CH:25]=3)[C:17]3[C:12](=[C:13]([F:18])[CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:19])=[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:20]3[CH:21]=[N:22][CH:23]=[N:24][CH:25]=3)[C:17]3[C:12](=[C:13]([F:18])[CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:19])=[N:10]2)[CH:3]=1

Participants

3

Reactant 2

HCID 49857442-Fluoro-3-methoxyphenylboronic acidHCID 585795331-(3-Bromo-4-fluorophenyl)-4-fluoro-1-(pyrimidin-5-yl)-1H-isoindol-3-amine

Product 1

HCID 462066401-(2',6-Difluoro-3'-methoxybiphenyl-3-yl)-4-fluoro-1-(pyrimidin-5-yl)-1H-isoindol-3-amineYield 18%

Procedure

The title compound was synthesized as described for Example 12 in 18% yield, starting from 1-(3-bromo-4-fluorophenyl)-4-fluoro-1-(pyrimidin-5-yl)-1H-isoindol-3-amine (59.6 mg, 0.15 mmol) and 2-fluoro-3-methoxybenzeneboronic acid (59.5 mg, 0.35 mmol); 1H NMR (500 MHz, DMSO-d6)6 ppm 9.08 (s, 1 H) 8.74 (s, 2 H) 7.81 (d, 1 H) 7.53-7.60 (m, 1 H) 7.42-7.49 (m, 1 H) 7.37 (dd, 1 H) 7.25-7.33 (m, 2 H) 7.18-7.25 (m, 2 H) 6.87-6.93 (m, 1 H) 6.77 (br. s., 2 H) 3.85 (s, 3 H). MS (ES−) m/z 445 [M−H]−

Sources & evidence

ORD record
ord-27f032616eb148ad938a28afda735f99
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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