3-Fluorophenylboronic acid → 3-{3-[(4,3'-Difluoro-biphenyl-3-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

HRID 1717094Notes

Reaction equation

HRID 1717094 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:16]=2[F:22])[CH:8]=1)[CH3:2].[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>>[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:15]2[CH:20]=[C:19]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([F:25])[CH:31]=3)[CH:18]=[CH:17][C:16]=2[F:22])=[O:23])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 684970723-[3-(5-Bromo-2-fluoro-benzoylamino)-phenyl]-acrylic acid ethyl ester

Product 1

HCID 684974073-{3-[(4,3'-Difluoro-biphenyl-3-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Procedure

The phenyl bromide (106) (100 mg, 0.25 mmol) was coupled to 3-fluoro-phenylboronic acid (39 mg, 0.28 mmol) using Method E. The crude product was purified by column chromatography eluting with 20% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude product was purified by column chromatography
  2. washeluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-d79cf1f43cf94790a0adb95991a0b60b
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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