Sodium Chloride → 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

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Reaction Steps

To a solution of 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (86.1 g) in DMF (860 mL) was added potassium tert-butoxide (87.5 g) with cooling in water bath. To the mixture was added ethyl iodide (122 g), and the mixture was stirred at room temperature for 6 h. The mixture was poured into EtOAc (1.2 L) and 5% aq. NaCl (1 L). The organic layer was separated. The aqueous layer was extracted with EtOAc (500 mL). The combined organic phase was washed with brine, dried over MgSO4, passed through a silica gel pad, and evaporated to give 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (88 g) as a black solid. This product was subjected to the next reaction without further purification.

Provenance & Evidence