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

HRID 2053268Notes

Reaction equation

HRID 2053268 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-62187c91ddfa44c5b5564e5fc7545fdc
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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