Ethyl 4-bromobenzoate → Ethyl 4-{{4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylphenyl}amino}benzoate

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of 11-ethyl-5,11-dihydro-8-[2-(4-amino-2-methylphenoxy)ethyl]-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (100 mg, 0.25 mmol), ethyl 4-bromobenzoate (61.0 μL, 0.37 mmol), t-BuONa (36.0 mg, 0.37 mmol), Pd2(dba)3 (2.5 mg, 2.7 μmol) and (+/−)-BINAP (5.0 mg, 8.0 1mol) in toluene (8 mL) was heated to 105° C. under nitrogen for 48 h. The cooled reaction mixture was diluted with EtOAc, filtered through a short pad of diatomaceous earth and was concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to give the title compound (55 mg, 40% yield) as a white solid.

Provenance & Evidence