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

HRID 1717090Notes

Reaction equation

HRID 1717090 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].[CH2:23]([O:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:33]3[CH:34]=[CH:35][CH:36]=[C:31]([O:30][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:32]=3)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27343133-Benzyloxy-phenylboronic acidHCID 684945603-{3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Product 1

HCID 684981583-(3-{[5-(3-Benzyloxy-phenyl)-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 3-benzyloxy-phenylboronic acid (69 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-9d2a85f617394030819b730afe646308
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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