Water → HCID 19360147, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (463 mg, 11.57 mmole, washed with pentane) in dry DMF (15 mL) was added 1-bromo-2-methylpropane (1.26 mL, 11.57 mmole), and thereafter a solution of 7-chloro-3-[(4-pyridinyl)amino]benzo[b]thiophene (2.87 g, 11.02 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 one hour and then heated to 60° C. An additional 232 mg of NaH and 0.63 mL of 1-bromo-2-methylpropane were added twice to drive the reaction to completion. The reaction mixture was then distributed between water and ethyl acetate, and the organic phase was washed with water, dried (MgSO4) and concentrated to obtain 3.07 g of a dark brown oil. This was flash chromatographed twice (silica, 5% MeOH/EtOAc then 10% MeOH/EtOAc; alumina, Et2O then EtOAc) to yield 2.02 g of product. The hydrochloride salt was formed in methanol with ethereal hydrogen chloride, concentrated to a solid and recrystallized from methanol and diethyl ether. The resulting white solid was dried for four hours under high vacuum over P2O5 and refluxing toluene to yield 1.61 g, mp 264° C. (dec.).

Provenance & Evidence