2-Fluoro-4-biphenylboronic Acid → 3-(3-{[5-(2-Fluoro-biphenyl-4-yl)-furan-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

HRID 2053213Notes

Reaction equation

HRID 2053213 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[O:17][C:18](Br)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)[CH3:2].[F:23][C:24]1[CH:29]=[C:28](B(O)O)[CH:27]=[CH:26][C:25]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:1]([O:3][C:4](=[O:22])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[O:17][C:18]([C:28]3[CH:27]=[CH:26][C:25]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[C:24]([F:23])[CH:29]=3)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27746982-Fluoro-4-biphenylboronic AcidHCID 684945603-{3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Product 1

HCID 684970123-(3-{[5-(2-Fluoro-biphenyl-4-yl)-furan-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

Conditions

Temperature
85 °C

Procedure

The furyl bromide (99)(100 mg, 0.28 mmol) was coupled to 2-Fluoro-biphenyl-4-boronic acid (65 mg, 0.30 mmol) acid using Method E, except that the reaction was heated at 85° C. The crude product was purified by column chromatography eluting with 20% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude product was purified by column chromatography
  2. washeluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-70972314ba4341f4b4115914075ed922
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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