5-Chloro-2-ethyl-9-methyl-13-(2-phenylethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one → 2-ethyl-9-methyl-13-(2-phenylethyl)-5-(1H-pyrrol-2-yl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

Participants

Reaction Conditions

Reaction Steps

A mixture containing 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(2-phenylethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.10 g, 0.26 mmol), potassium acetate (0.05 g, 0.51 mmol), N-(tert-butyloxycarbonyl)pyrrole (0.078 g, 0.47 mmol), and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol) in 2 mL of N,N-dimethylformamide was heated in a sealed tube at 125° C. for 10 hours. Additional potassium acetate (50 mg), N-(tert-butyloxycarbonyl)pyrrole (0.08 g), and tetrakis(triphenylphosphine)palladium(0) (15 mg) were added, and the reaction mixture was heated at 140° C. for an additional 8 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated. Purification by flash chromatography, eluting with ethyl acetate/hexanes, provided 20 mg of the title compound, as a foam.

Provenance & Evidence