3-Amino-3-cyclopropyl-acrylic acid ethyl ester → 2-Cyclopropyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-nicotinic acid ethyl ester

HRID 890500Notes

Reaction equation

HRID 890500 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH:5]=[C:6]([NH2:10])[CH:7]1[CH2:9][CH2:8]1)[CH3:2].[F:12][C:13]([F:31])([F:30])/[C:14](/O)=[CH:15]/[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)=O>>[CH2:1]([O:3][C:4](=[O:11])[C:5]1[C:14]([C:13]([F:12])([F:31])[F:30])=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:20][CH:19]=2)=[N:10][C:6]=1[CH:7]1[CH2:8][CH2:9]1)[CH3:2]

Participants

3

Reactant 2

HCID 534018893-Amino-3-cyclopropyl-acrylic acid ethyl esterHCID 178520888HCID 178520888, compound

Product 1

HCID 865977892-Cyclopropyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-nicotinic acid ethyl ester

Procedure

In analogy to the procedure described in example 18 d], 3-amino-3-cyclopropyl-acrylic acid ethyl ester (J. P. Célérier, E. Deloisy, P. Kapron, G. Lhommet, P. Maitte, Synthesis 1981, 130–133) was reacted with (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethoxy-phenyl)-but-2-en-1-one (example 16 a]) to give the title compound as colorless oil.

Workup

  1. customdescribed in example 18 d

Sources & evidence

ORD record
ord-a879d498895945cb8b7af417867b5ebf
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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