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

HRID 2053282Notes

Reaction equation

HRID 2053282 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:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=3)[CH:18]=[CH:17][C:16]=2[F:22])=[O:23])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 40356283[3-(5-Bromo-2-fluoro-benzoylamino)-phenoxy]-acetic acid ethyl ester

Product 1

HCID 59654610{3-[(4,4'-Difluoro-biphenyl-3-carbonyl)-amino]-phenoxy}-acetic acid ethyl ester

Procedure

The phenyl bromide (139)(100 mg, 0.25 mmol) was coupled to 4-fluoro-phenylboronic acid (33 mg, 0.23 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-c94c4c3fe1b94400acd482b85930839a
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

Loading…