4-Fluoroaniline → 2-azido-4-bromo-N-(4-fluorophenyl)-benzamide

Participants

Role	Name	HCID	Charge
Reactant	4-Fluoroaniline	HCID 9731	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-Azido-4-bromobenzoic acid	HCID 86051548	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-azido-4-bromo-N-(4-fluorophenyl)-benzamide	HCID 86666421	91.5%

Reaction Steps

To a stirred solution of compound (xi) (15 g, 61.98 mmol) in DMF (150 mL) was added HATU (28.28 g, 74.34 mmol) at 0° C. The reaction mixture was stirred for 15 min and DIPEA (16.01 mL, 92.26 mmol) was added followed by 4-fluoroaniline (7.57 g, 68.68 mmol) at the same temperature. The reaction mixture was allowed to warm to RT and stirring was continued for 16 h. The reaction was then poured into cold water (500 mL) and stirred for 15 min. The solid was filtered and washed with water (3×100 mL) and dried (Na2SO4) to give 2-azido-4-bromo-N-(4-fluorophenyl)-benzamide (xii) (19 g, 91%) as an off-white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546389B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-0472fff3a68e4da7a82a016b8149fc49
Source note	uspto-grants-2013_10