1,2-Dimethoxyethane → 9-tert-butyl-3-methoxy-2-pyridin-3-yl-15-(1,3-thiazol-5-yl)-5,6,9,10,11,12-hexahydro[1,5]oxazonino[8',7':4,5]pyrrolo[2,1-a]isoquinolin-8(14H)-one

Participants

Reaction Steps

A solution of 75 mg of 8e, 35 mg of pyridine-3-boronic acid, 60 mg of K2CO3 in 2 ml of degassed 90% aq. dimethoxyethane was heated at 90° C. for 16 h The reaction mixture was cooled, diluted with water and extracted with ethyl acetate. The organic layer was once washed with 1M K2CO3, once with water, dried and concentrated. The crude material was chromatographed over silica gel using a gradient of toluene/acetone. The isolated material was treated with diethyl ether and provided 70 mg of 8f; Mp 200-201° C.; Rf 0.15 (toluene/acetone 7/3). MS-ESI: [M+1] 529.3.

Provenance & Evidence