3-Aminocinnamic acid ethyl ester → 3-(3-{[6-(4-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

HRID 1717146Notes

Reaction equation

HRID 1717146 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:30])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=1)[CH3:18]>>[CH2:17]([O:19][C:20](=[O:30])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:14]([C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:13]=2)=[O:16])[CH:24]=1)[CH3:18]

Participants

3

Reactant 2

HCID 978253-Aminocinnamic acid ethyl esterHCID 210817086-(4-Fluorophenyl)picolinic acid

Product 1

HCID 684969113-(3-{[6-(4-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

Procedure

Carboxylic acid (152) (50 mg, 0.23 mmol) was coupled to aniline (60) (44 mg, 0.23 mmol) using Method C. The crude residue was purified by column chromatography eluting with 10% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude residue was purified by column chromatography
  2. washeluting with 10% EtOAc in heptane

Sources & evidence

ORD record
ord-1ff8dd44a795432fa2958c1b99b37a2b
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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