4-Bromo-2-chloro-5-(trifluoromethyl)aniline → N-(4-bromo-2-chloro-5-trifluoromethyl-phenyl)-6-fluoro-nicotinamide

HRID 1504307Notes

Reaction equation

HRID 1504307 reaction equation
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][N:16]=1>C(Cl)Cl.CC(N(C)C)=O>[Br:12][C:5]1[C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]([NH:1][C:21](=[O:22])[C:18]2[CH:19]=[CH:20][C:15]([F:14])=[N:16][CH:17]=2)=[C:3]([Cl:13])[CH:4]=1

Participants

5

Reactant 2

HCID 140993984-Bromo-2-chloro-5-(trifluoromethyl)anilineHCID 146236022-Fluoropyridine-5-carbonyl chloride

Product 1

HCID 87422108N-(4-bromo-2-chloro-5-trifluoromethyl-phenyl)-6-fluoro-nicotinamide

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-2-bromo-4-chlorobenzotrifluoride (466 mg, 1.70 mmol) dissolved in DCM (1 mL) was slowly added a solution of 2-fluoropyridine-5-carbonyl chloride (270 mg, 1.70 mmol) in DCM (1 mL). A few drops of DMA were added and the reaction mixture was concentrated to form N-(4-bromo-2-chloro-5-trifluoromethyl-phenyl)-6-fluoro-nicotinamide as a purple solid.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c21fcc794d2d4027a7fc7feeb619f3b0
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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