Triethylamine → N-(2-Amino-5-fluoro-phenyl)-5-bromo-2-chloro-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	5-Bromo-2-chlorobenzoic acid	HCID 33127	—
Reactant	4-Fluorobenzene-1,2-diamine	HCID 164584	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(2-Amino-5-fluoro-phenyl)-5-bromo-2-chloro-benzamide	HCID 63257336	69%

Reaction Steps

Method 3,4—Step a To a mixture of the solids 5-Bromo-2-chlorobenzoic acid (7.00 g, 29.79 mmol), 4-Fluoro-benzene-1,2-diamine (4.65 g, 36.94 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (11.89 g, 31.28 mmol), triethylamine (TEA) (4.60 mL, 32.77 mmol), dichloromethane (120 mL) and dimethylformamide (DMF) (30 mL) were added. The reaction mixture was stirred at room temperature overnight, water was added (30 mL) and stirred until the formation of a precipitate. The precipitate was filtered off, washed with dichloromethane (3×10 mL) and dried to afford 6.90 g of the title compound (69%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08835648B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-b8fafa47562a4f1b80cb580c176203c0
Source note	uspto-grants-2014_09