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

HRID 1444376Notes

Reaction equation

HRID 1444376 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-8844c3f3d732400b8926495427e5bad2
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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