Water → HCID 19360255, compound

Participants

Reaction Steps

To a suspension of NaH (452 mg, 11.29 mmole, washed with pentane) in dry DMF (15 mL) was added 1-bromopropane (1.03 mL, 11.29 mmole), and thereafter a solution of 7-chloro-3-[(4-pyridinyl)amino]benzo[b]thiophene (2.8 g, 10.75 mmole) in warm DMF (20 mL) was added so that the reaction mixture was warm to the touch. After the addition, the reaction mixture was stirred for two hours, distributed between water and ethyl acetate, and the organic phase was washed with water, dried (MgSO4) and concentrated to afford 3.07 g of a dark brown oil. This was flash chromatographed twice (silica, 5% MeOH/EtOAc then 10% MeOH/EtOAc; alumina, Et2O) to yield 2.36 g of product. The hydrochloride salt was formed in methanol with ethereal hydrogen chloride, the solution was concentrated to a solid and the solid was recrystallized from methanol and diethyl ether. The resulting pale yellow solid was dried for four hours under high vacuum over P2O5 and refluxing toluene to yield 1.77 g, mp 249° C. (dec.).

Provenance & Evidence