3-Chloro-5-fluorobenzoic acid → 3-Chloro-5-fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-benzamide

HRID 878098Notes

Reaction equation

HRID 878098 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]([F:26])[CH:25]=1)[C:20]([OH:22])=O>CCCCCCC.CCOC(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([F:26])[CH: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

4

Reactant 2

HCID 27348403-Chloro-5-fluorobenzoic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 706633703-Chloro-5-fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3-chloro-5-fluorobenzoic acid (CAS RN 25026-64-6) and using a gradient of n-heptane:EtOAc (100:0 to 30:70) for the chromatographic purification. Yellow solid (17%). MS (ESI): m/z=355.10 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-f2c89beae8e1432691acb382d43de154
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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