3,5-Dichlorophenylboronic acid → (3-{[5-(3,5-Dichloro-phenyl)-furan-2-carbonyl]-amino}-phenyl)-acetic acid methyl ester

HRID 2053123Notes

Reaction equation

HRID 2053123 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[O:15][C:16](Br)=[CH:17][CH:18]=2)=[O:13])[CH:6]=1.[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([Cl:28])[CH:27]=1>>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[O:15][C:16]([C:24]3[CH:23]=[C:22]([Cl:21])[CH:27]=[C:26]([Cl:28])[CH:25]=3)=[CH:17][CH:18]=2)=[O:13])[CH:6]=1

Participants

3

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 59654700(3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl)-acetic Acid Methyl Ester

Product 1

HCID 59654620(3-{[5-(3,5-Dichloro-phenyl)-furan-2-carbonyl]-amino}-phenyl)-acetic acid methyl ester

Procedure

Methyl ester (16) (100 mg, 0.30 mmol) was coupled to 3,5-dichloro-phenylboronic acid (61 mg, 0.33 mmol) using Method E. The crude compound was purified by column chromatography, eluting in 17% EtOAc in heptane to give the title compound. Yield: 11 mg, 9%; LC/MS tr 1.76 min; MS(ES+) m/z 404, 406 (M+H)

Workup

  1. customThe crude compound was purified by column chromatography
  2. washeluting in 17% EtOAc in heptane

Sources & evidence

ORD record
ord-e629777a900a4976a9d6d153a199905b
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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