3-Fluorophenylboronic acid → 3-(3-{[5-(3-Fluoro-phenyl)-furan-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

HRID 1444305Notes

Reaction equation

HRID 1444305 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:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=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][CH:25]=[C:24]([F:23])[CH:29]=3)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 684945603-{3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Product 1

HCID 684952193-(3-{[5-(3-Fluoro-phenyl)-furan-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

Procedure

The furyl bromide (99) (125 mg, 0.34 mmol) was coupled to 3-fluoro-phenylboronic acid (48 mg, x 0.41 mmol) acid using Method E. The residue was purified by column chromatography eluting with 20% EtOAc in heptane to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-5baa1420df1a4da9ba4607a97a28bcaf
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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