Cesium carbonate → HCID 10274713, compound

Participants

Reaction Steps

Preparation of 2-[(1-cyclohexylmethyl-2-methyl-1H-benz[g]indol-4-yl)oxy]acetic acid methyl ester. A solution of 1-cyclohexylmethyl-2-methyl-4-methoxybenz[g]indole (0.46 g, 1.5 mmol) in methylene chloride (14 mL) was cooled to 0° C. and treated with boron tribromide (0.35 mL, 3.7 mmol) in portions over 5 min. The mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was poured onto ice and water and the resulting solution extracted with chloroform. The organic layer was washed once with water, once with dilute sodium bicarbonate solution, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (10 mL) and treated with methyl bromoacetate (0.17 mL, 1.8 mmol) and cesium carbonate (0.64 g, 1.8 mmol) at room temperature with stirring for 29 h. The mixture was diluted with water and extracted three times with ethyl acetate. The combined ethyl acetate fractions were washed once with water, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 10% ethyl acetate/90% hexanes) of the residue provided 0.23 g (42%) of the title compound as a white fibrous solid: mp 156-158° C. 1H NMR (CDCl3) δ8.11 (d, J=8.4 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.42 (t, J=6.6 Hz, 1H), 7.33 (t, J=7.0 Hz, 1H), 6.66 (s, 1H), 6.58 (s, 1H), 4.87 (s, 2H), 4.27 (d, J=7.3 Hz, 2H), 3.82 (s, 3H), 2.49 (s, 3H), 2.05 (bs, 1H), 1.68 (m, 5H), 1.12 (m, 5H); MS ES+ m/e 366 (p+1); IR (KBr, cm−1) 2928, 1757, 1210.

Provenance & Evidence