Diisopropylethylamine → 2-Fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

HRID 877962Notes

Reaction equation

HRID 877962 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([N:16]([CH3:15])[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 601969942-Fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-5-trifluoromethylbenzoyl chloride (80 mg, 0.35 mmol, CAS RN 207981-46-2) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (35 mg, 0.18 mmol, example 1, intermediate a) and DIPEA (92 μL, 0.53 mmol) in CH2Cl2 (1 mL). The reaction mixture was stirred overnight and then loaded directly onto a silica gel column and eluted with 50% EtOAc in n-hexane to yield the desired product as a waxy solid (36 mg, 53%). MS (ESI): m/z=389.0 [M+H]+.

Workup

  1. washeluted with 50% EtOAc in n-hexane

Sources & evidence

ORD record
ord-a5b8a6d7e465430e8b04ad9c7060114f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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