2-Chloro-6-(trifluoromethyl)pyridine-4-carboxylic acid → HCID 86670781, compound

HRID 878194Notes

Reaction equation

HRID 878194 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=1)[C:20]([OH:22])=O>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=1)[C:20]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:22]

Participants

3

Reactant 2

HCID 112183892-Chloro-6-(trifluoromethyl)pyridine-4-carboxylic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 86670781HCID 86670781, compound

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 2-chloro-6-trifluoromethyl-isonicotinic acid (prepared in analogy to F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2004, 18, 3793-3798) after a reaction time of 66 hours. The compound was purified by two silica gel chromatographies (10 g column each, gradient of n-heptane:EtOAc (100:0 to 50:50) for the first and EtOAc for the second chromatography), followed by preparative HPLC (phenomenex gemini column, gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2)). Colorless foam (49%). MS (ESI): m/z=406.09 [M+H]+.

Workup

  1. customThe compound was purified by two silica gel chromatographies (10 g column each, gradient of n-heptane:EtOAc (100:0 to 50:50) for the first and EtOAc for the second chromatography),

Sources & evidence

ORD record
ord-40c205d19c504511ba35fe765e716233
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…