2-Bromo-5-(trifluoromethyl)pyridine → N-(4-chloro-3-(5-(trifluoromethyl)pyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide

HRID 1364652Notes

Reaction equation

HRID 1364652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[N:12][C:11]=2[CH3:20])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:34]=[CH:35][C:36](Br)=[N:37][CH:38]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:17])[F:19])=[N:12][C:11]=2[CH3:20])=[CH:4][C:3]=1[C:36]1[CH:35]=[CH:34][C:33]([C:32]([F:41])([F:40])[F:31])=[CH:38][N:37]=1

Participants

3

Reactant 2

HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 66896658N-(4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide

Product 1

HCID 58614839N-(4-chloro-3-(5-(trifluoromethyl)pyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide

Procedure

N-(4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide (˜0.5 mmol) was used in Procedure A with 5-trifluoromethyl-2-bromopyridine (113 mg, 0.5 mmol). Purified by silica gel chromatography (5-50% ethyl acetate/hexanes) to yield N-(4-chloro-3-(5-(trifluoromethyl)pyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide as a white foam: TLC Rf=0.30 (15% ethyl acetate/hexanes); MS (Q1) 460 (M)+.

Workup

  1. customPurified by silica gel chromatography (5-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3c514e104ce34611b1ba8889b6167b56
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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