1,2-Dimethoxyethane → 9-tert-butyl-2-(3-pyridyl)-14-bromo-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 250 mg of 25a, 72 mg of pyridine-3-boronic acid, 135 mg of K2CO3 and 5 ml of degassed 90% aqueous DME was heated under N2 for 16 h at 90° C. The reaction was then cooled and diluted with water, and the product was extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated, and the remainder was chromatographed over silica gel (using a gradient of heptane/ethyl acetate as eluent). The product isolated was triturated with diethylether, to provide 183 mg of 25b; NMR (CDCl3) δ 8.85, 8.56, 7.91, and 7.35 (4×m, 4, pyridyl-H), 8.37 and 6.87 (2×s, 2, Ar—H), 4.45 and 3.40-3.90 (br.m, 4, 2×CH2), 3.05 (bm, 2, CH2), 2.60 (br.m, 2, CH2), 1.90 and 1.70 (2×br.m, 4, 2×CH2), 1.58 (s, 9, tertC4H9).

Provenance & Evidence