Bromobenzene → HCID 68670937, compound

Participants

Reaction Conditions

Reaction Steps

In a dry Schlenk tube under argon atmosphere tert-butyl 2-amino-4-(4-methylpiperazin-1-yl)benzoate (800 mg, 2.745 mmol) was dissolved in dry toluene (14 mL) Argon was bubbled through the mixture for a few minutes before adding bromobenzene (0.32 mL, 3.02 mmol, 1.1 eq), Cs2CO2 (1.34 g, 4.118 mmol, 1.5 eq), Pd(OAc)2 (16 mg, 0.069 mmol, 2.5 mol %) and Rac-BINAP (88 mg, 0.137 mmol, 5 mol %). The mixture was then stirred at 100° C. for 21 hours. The mixture was allowed to cool to room temperature and diluted with dichloromethane. Salts were filtered over a Celite pad and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography over silica gel (DCM/EtOH/NH3 7% in methanol 95:5:0.5) to give 1.13 g of title compound (quant. yield) as off-white solid

Provenance & Evidence