2-chloro-5,11-dihydro-11-ethyl-8-[trans-2-(4-pyridyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one → 5-Chloro-2-ethyl-9-methyl-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

Participants

Reaction Steps

To a mixture of 2-chloro-5,11-dihydro-11-ethyl-8-[trans-2-(4-pyridyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (2.3 g, 5.9 mmol) and palladium black (0.25 g) in 30 mL of 1,4-dioxane was added a solution of sodium hypophosphite (0.82 g 7.7 mmol) in 15 mL of water. The reaction mixture was heated at 80°-90° C. for 3 hours. The reaction mixture was then filtered through Celite and extracted with ethyl acetate. The product was purified by chromatography over silica gel, eluting with methanol/dichloromethane, and recrystallized from ethyl acetate/hexanes to give 1.75 g of the title compound as colorless crystals, m.p. 158°-159° C.

Provenance & Evidence