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

HRID 2053280Notes

Reaction equation

HRID 2053280 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. For the ester: LC/MS tr 1.62 min; MS(ES+) m/z 412 (M+H)

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-76be9de7c11b4505b62e0bfa1cb75589
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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