3-Methyl-5-(trifluoromethyl)benzoic acid → 3,N-Dimethyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

HRID 878103Notes

Reaction equation

HRID 878103 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].[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:20]([OH:22])=O>>[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[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

3

Reactant 2

HCID 27755883-Methyl-5-(trifluoromethyl)benzoic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 601970023,N-Dimethyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

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-methyl-5-(trifluoromethyl)benzoic acid (CAS RN 117186-02-4) after a reaction time of 67 hours. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). Light brown oil (9%). MS (ESI): m/z=385.15[M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 30:70)

Sources & evidence

ORD record
ord-0056a2784c2c49aa88185b099b2637f7
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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