Potassium Carbonate → 9-tert-butyl-3-methoxy-2-pyridin-3-yl-14-(1,3-thiazol-5-yl)-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Participants

Reaction Steps

A degassed solution of 40 mg of 11i, 20 mg of pyridyl-3-boronic acid, 30 mg of K2CO3, 12 mg Pd(PPh3)4 and 3 ml of 90% aq. dimethoxyethane was heated at 90° C. for 16 hr. The reaction mixture was cooled, poured into 20 ml of 1N NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried, concentrated and the residues were passed through a short silica column, using a gradient of toluene/acetone as eluent. The isolated material was treated with diethyl ether and gave 35 mg of 11j as white crystals; Mp: 227-229° C.; Rf 0.35 (toluene/acetone 1/1).

Provenance & Evidence