Potassium Carbonate → 9-tert-butyl-2-pyridin-3-yl-13-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 150 mg of 13c, 44 mg of pyridine-3-boronic acid, 80 mg of K2CO3 and 22 mg of Pd(PPh3)4 in 3 ml of degassed dimethoxyethane was heated at 90° C., for 16 hr. The reaction mixture was cooled and diluted with 20 ml of water and the product was extracted with ethyl acetate. The extract was washed once with 2N KOH and once with water, dried and concentrated. The crude material was chromatographed over silica gel, using a gradient of heptane/ethyl acetate as eluent. The product isolated was triturated with pentane, to provide 95 mg of 13d as white, crystalline material. Mp 184-186° C. Rf 0.25 (heptane/ethyl acetate 1/1). MS-ESI: [M+1] 494.11 and 496.11.

Provenance & Evidence