Cesium carbonate → (s)-Tert-butyl 2-((7-(4-(benzyloxy)-2-oxopyridin-1(2h)-yl)-5-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-2(5h)-yl)methyl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-tert-butyl-2-(bromomethyl)pyrrolidine-1-carboxylate (0.45 g, 1.7 mmol) in DMSO (1.5 mL) was added to a solution of 4-(benzyloxy)-1-(9-methyl-2,3,4,9,-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridine-2(1H)-one (0.33 g, 0.85 mmol), and Cs2CO3 (1.10 g, 3.4 mmol) in DMSO (2.8 mL), and the resulting solution was heated at 60° C. for 18 h. The reaction mixture was diluted with H2O and extracted with CH2Cl2 (3×25 mL). The combined organic extracts were washed with brine (2×25 mL), dried over Na2SO4 and concentrated to dryness under reduced pressure. Purification by flash column chromatography (40 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 hold 5 column volumes, increased to 0:100:0 over 20 column volumes) provided a clear film. The film was diluted with EtOAc and washed with brine (4×10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound (19 mg, 3%) as a clear film: ESI MS m/z 569 [M+H]+.

Provenance & Evidence