Dimethylformamide → HCID 10223886, compound

Participants

Reaction Steps

A solution of 1-benzyl-2-methyl-4-methoxy-1,6,7,8-tetrahydrocyclopent[g]indole (2.2 g, 7.6 mmol) in chloroform (40 mL) was treated with boron tribromide (2.8 mL, 30 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 2.5 h. The mixture was poured into water and extracted with chloroform. The organic layer was washed once with water, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo to provide an oil. A solution of this material (oil) in N,N-dimethylformamide (35 mL) was treated with cesium carbonate (3.21 g, 9.10 mmol) and methyl bromoacetate (0.86 mL, 9.1 mmol) at room temperature. After stirring for 18 h, the mixture was poured into water and extracted with ethyl acetate. The organic layer was 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) provided 0.43 g (16%) of the title product as a white solid: mp 135-138° C. 1H NMR (CDCl3) δ 7.22 (m, 3H), 6.88 (d, J=7.0 Hz, 2H), 6.47 (s, 1H), 6.36 (s, 1H), 5.42 (s, 2H), 4.76 (s, 2H), 3.82 (s, 3H), 3.00 (t, J=7.3 Hz, 2H), 2.90 (t, J=7.3 Hz, 2H), 2.29 (s, 3H), 2.04 (quintet, J=7.0 Hz, 2H); MS ES+ m/e 350 (p+1); IR (CHCl3, cm−1) 2955, 1760, 1737, 1496.

Provenance & Evidence