Diisopropylethylamine → N-(6-Methoxy-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 877972Notes

Reaction equation

HRID 877972 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].[CH3:18][O:19][C:20]1[N:25]=[CH:24][C:23]([NH:26][CH3:27])=[C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:21]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:18][O:19][C:20]1[N:25]=[CH:24][C:23]([N:26]([CH3:27])[C:6](=[O:7])[C:5]2[CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)=[C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 706633806-methoxy-N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 60197191N-(6-Methoxy-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Bis-trifluoromethylbenzoyl chloride (126 μL, 0.69 mmol, CAS RN 1271-19-8) was added to a solution of 6-methoxy-N-methyl-4-o-tolylpyridin-3-amine (105 mg, 0.46 mmol) and DIPEA (240 μL, 1.38 mmol) in CH2Cl2 and stirred for 2 h. The reaction mixture was then loaded directly onto a silica gel column Elution with 20% EtOAc in n-hexane gave the title product as a colorless foam (161 mg, 76%). MS (ESI): m/z=469.0 [M+H]+.

Workup

  1. washThe reaction mixture was then loaded directly onto a silica gel column Elution with 20% EtOAc in n-hexane

Sources & evidence

ORD record
ord-110027cab62e41e3be0864dc2cf2f8f1
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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