3,5-Bis-trifluoromethylphenylboronic acid → 3-(3-{[5-(3,5-Bis-trifluoromethyl-phenyl)-furan-2-carbonyl]-amino}phenyl)-acrylic acid ethyl ester

HRID 2053210Notes

Reaction equation

HRID 2053210 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]([F:39])([F:38])[C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=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:27]3[CH:28]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:30]=[C:25]([C:24]([F:23])([F:39])[F:38])[CH:26]=3)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 684945603-{3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Product 1

HCID 723488113-(3-{[5-(3,5-Bis-trifluoromethyl-phenyl)-furan-2-carbonyl]-amino}phenyl)-acrylic acid ethyl ester

Conditions

Temperature
100 °C

Procedure

The furyl bromide (99)(70 mg, 0.19 mmol) was coupled to 3,5-bis-trifluoromethyl-phenylboronic acid (55 mg, 0.21 mmol) acid using Method E, except that the reaction was heated at 100° C. The crude product was purified by column chromatography eluting with a stepped gradient of 0-10% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude product was purified by column chromatography
  2. washeluting with a stepped gradient of 0-10% EtOAc in heptane

Sources & evidence

ORD record
ord-ed1818f76bf24b4e98a40da25257b5e0
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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