Cesium carbonate → HCID 23405921, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-bromobenzyl)-2-methyl-4-methoxy-1,6,7,8-tetrahydrocyclopent[g]indole (1.28 g, 3.40 mmol) in methylene chloride (20 mL) was cooled in an ice/methanol bath and treated with boron tribromide (0.65 mL, 6.9 mmol). The mixture was warmed to −10° C. over 1.5 h then diluted with methanol (2 mL) and excess saturated aqueous sodium bicarbonate solution. The aqueous layer was separated and extracted with a fresh portion of methylene chloride. The combined methylene chloride layers were washed once with water, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in methylene chloride and filtered through a pad of silica gel. The filtrate was concentrated in vacuo and the residue dissolved in N,N-dimethylformamide (5 mL) and treated with cesium carbonate (1.00 g, 3.06 mmol) and methyl bromoacetate (0.29 mL, 3.1 mmol) at room temperature for 20 h. The mixture was concentrated in vacuo via vacuum transfer and the residue dissolved in methylene chloride and filtered through a pad of silica gel. The filtrate was concentrated in vacuo. Chromatography (silica gel, methylene chloride/hexanes) of the residue provided 1.10 g (84%) of the title compound. 1H NMR (CDCl3) δ 7.59 (m, 1H), 7.07 (m, 2H), 6.47 (s, 1H), 6.33 (s, 1H), 6.18 (m, 1H), 5.35 (bs, 2H), 4.74 (s, 3H), 3.80 (s, 3H), 2.86 (m, 4H), 2.26 (s, 3H), 1.99 (quintet, J=7.3 Hz, 2H); MS ES+ m/e 428, 430 (p+1).

Provenance & Evidence