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

HRID 633035Notes

Reaction equation

HRID 633035 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]1[CH:33]=[CH:34][C:35](Br)=[N:36][CH:37]=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:19])[F:17])=[N:12][C:11]=2[CH3:20])=[CH:4][C:3]=1[C:35]1[CH:34]=[CH:33][C:32]([F:31])=[CH:37][N:36]=1

Participants

3

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 66896658N-(4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide

Product 1

HCID 58614924N-(4-chloro-3-(5-fluoropyridin-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 (˜1 mmol) was used in Procedure A with 5-fluoro-2-bromopyridine (1 mmol). Purified by silica gel chromatography (5-45% ethyl acetate/hexanes) to yield N-(4-chloro-3-(5-fluoropyridin-2-yl)phenyl)-2-methyl-6-(trifluoromethyl)nicotinamide as a tan solid:

Workup

  1. customPurified by silica gel chromatography (5-45% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2642385696a04289a7c8b646819d973f
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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