3-Aminocinnamic acid ethyl ester → 3-[3-(5-Bromo-2-fluoro-benzoylamino)-phenyl]-acrylic acid ethyl ester

HRID 2053257Notes

Reaction equation

HRID 2053257 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:12]([O:14][C:15](=[O:25])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1)[CH3:13]>>[CH2:12]([O:14][C:15](=[O:25])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[F:11])[CH:19]=1)[CH3:13]

Participants

3

Reactant 2

HCID 978253-Aminocinnamic acid ethyl esterHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 684970723-[3-(5-Bromo-2-fluoro-benzoylamino)-phenyl]-acrylic acid ethyl ester

Procedure

5-Bromo-2-fluoro-benzoic acid (250 mg, 1.14 mmol) was coupled to aniline (60)(240 mg, 1.26 mmol) using Method D. The residue was purified by column chromatography eluting with a stepped gradient of 10-15% EtOAc in heptane to give the title compound.

Workup

  1. customThe residue was purified by column chromatography
  2. washeluting with a stepped gradient of 10-15% EtOAc in heptane

Sources & evidence

ORD record
ord-a6b70924b5764262b5276b9585aa4049
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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