Phenylboronic Acid → (3-[(4-Chloro-biphenyl-3-carbonyl)-amino]-phenyl)-acetic acid ethyl ester

HRID 2053143Notes

Reaction equation

HRID 2053143 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=2[Cl:21])[CH:7]=1)[CH3:2].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:14]2[CH:19]=[C:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:17]=[CH:16][C:15]=2[Cl:21])=[O:22])[CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 59654675[3-(5-Bromo-2-chlorobenzoylamino)phenyl]acetic acid ethyl ester

Product 1

HCID 59654748(3-[(4-Chloro-biphenyl-3-carbonyl)-amino]-phenyl)-acetic acid ethyl ester

Conditions

Temperature
80 °C

Procedure

[3-(5-Bromo-2-chloro-benzoylamino)-phenyl]-acetic acid ethyl ester (198 mg, 0.50 mmol) was coupled to phenylboronic acid using Method E, except that the reaction mixture was heated at 80° C. for 25 min. The crude product was purified by column chromatography using 20% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a58417df8caf4b50af8825d314ab4482
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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