Benzyl Bromide → 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-phenylmethoxy-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

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Reaction Conditions

Reaction Steps

The 2-chloro-5,11-dihydro-11-ethyl-8-hydroxy-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.052 g, 0.17 mmol) was dissolved in tetrahydrofuran and treated with excess sodium hydride (60% wt.) followed by benzyl bromide (0.04 mL, 0.34 mmol). After 24 hours stirring the mixture was cooled to 0° C. and the excess sodium hydride was quenched by the dropwise addition of water and the resulting solution was extracted with dichloromethane (3×20 mL) The combined organics were dried over magnesium sulfate, concentrated and the residue was purified by chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) followed by crystallization from hexanes to give the title compound (0.035 g, 52%), m.p. 159°-160° C.

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