2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → N-(4-o-Tolyl-pyridin-3-yl)-N-(2,2,2-trifluoro-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide

HRID 878157Notes

Reaction equation

HRID 878157 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH:13][CH2:14][C:15]([F:18])([F:17])[F:16].[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[N:30]=1)[C:25](O)=[O:26]>>[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N:13]([CH2:14][C:15]([F:16])([F:17])[F:18])[C:25](=[O:26])[C:24]1[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[N:30]=[C:22]([C:21]([F:36])([F:20])[F:35])[CH:23]=1

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 70663500(4-o-Tolyl-pyridin-3-yl)-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 86670761N-(4-o-Tolyl-pyridin-3-yl)-N-(2,2,2-trifluoro-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide

Procedure

The title compound was prepared in analogy to example 90, from (4-o-tolyl-pyridin-3-yl)-(2,2,2-trifluoro-ethyl)-amine and 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 23 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 50:50). Light brown solid (26%). MS (ESI): m/z=508.11 [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 50:50)

Sources & evidence

ORD record
ord-a77910c3f4e24befadcd00555b9d0d9f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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