2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-2,6-bis-trifluoro methyl-isonicotinamide

HRID 878154Notes

Reaction equation

HRID 878154 reaction equation
FC1[CH:3]=[C:4]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])C=1)[C:5]([N:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[O:22][CH3:23])[CH3:8])=[O:6].[F:31][C:32]([F:47])([F:46])[C:33]1C=C(C=C(C(F)(F)F)[N:41]=1)C(O)=O>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:7]([CH3:8])[C:5](=[O:6])[C:4]2[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:41]=[C:33]([C:32]([F:47])([F:46])[F:31])[CH:3]=2)=[C:16]([O:22][CH3:23])[CH:17]=1

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 70663278HCID 70663278, compound

Product 1

HCID 86670760N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-2,6-bis-trifluoro methyl-isonicotinamide

Procedure

The title compound was prepared in analogy to example 90, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine (example 129, intermediate) and 2,6-bis(trifluoromethyl) isonicotinic acid (Key Organics Ltd.) after a reaction time of 22 hours. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown solid (73%). MS (ESI): m/z=474.11 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-b27d6b8e876e455790b23974fe1bb583
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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