3-Fluorophenylboronic acid → (3-[(4,3'-Difluoro-biphenyl-3-carbonyl)-amino]-phenoxy}-acetic Acid Ethyl Ester

HRID 1717158Notes

Reaction equation

HRID 1717158 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O: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])[CH2:5][O: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 40356283[3-(5-Bromo-2-fluoro-benzoylamino)-phenoxy]-acetic acid ethyl ester

Product 1

HCID 59654725(3-[(4,3'-Difluoro-biphenyl-3-carbonyl)-amino]-phenoxy}-acetic Acid Ethyl Ester

Procedure

The phenyl bromide (139) (100 mg, 0.25 mmol) was coupled to 3-fluoro-phenylboronic acid (34 mg, 0.24 mmol) using Method E. During this reaction, partial hydrolysis occurred. The residue was extracted using Work-up E1 to give a mixture of acid and ester, which was used without further purification.

Workup

  1. customDuring this reaction, partial hydrolysis
  2. extractionThe residue was extracted
  3. customto give
  4. customwas used without further purification

Sources & evidence

ORD record
ord-2d9efe2ba5504a718ce84d5490fc1bd4
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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