Ethyl Acetate → HCID 11669602, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine (10.0 g), methanesulfonic acid 3-cyanomethyl-5-methanesulfonyloxy-pentyl ester (11.3 g) and N,N-diisopropylethylamine (8.25 g) in N-methylpyrrolidone (10 mL) was heated at 135° C. for 4 hours. Methanesulfonic acid 3-cyanomethyl-5-methanesulfonyloxy-pentyl ester (2.60 g) was added to the reaction mixture and the mixture was heated at 135° C. for 4.5 hours. After cooling to room temperature, the reaction mixture was poured into a mixture of ethyl acetate, hexane and water (10/1/3), and separated. The aqueous phase was extracted with a mixture of ethyl acetate and hexane (10/1). The combined organic phase was washed with brine, dried over MgSO4, and filtered, and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate:CHCl3=4/1/0.5) to obtain a solid. The solid was crystallized from diisopropylether to obtain {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile (8.61 g) as a solid.

Provenance & Evidence