Pentane → 4-Benzoyl-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine

Participants

Reaction Conditions

Reaction Steps

4-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.345 g, 1.0 mmol), was dissolved in 10 ml of dry tetrahydrofuran under a nitrogen atmosphere, and the solution was cooled to -78° C., while 1.35 M t-butyllithium in pentane (1.5 ml, 2.03 mmol) was added slowly. The orange solution was stirred for 30 minutes at -78° C. N,N-dimethylbenzamide (0.19 g, 1.27 mmol) dissolved in 5 ml of tetrahydrofuran was added and the reaction was stirred for 20 minutes. The reaction mixture was heated to room temperature, and stirred for 2 days. The mixture was poured into 50 ml of a saturated ammonium chloride solution and the organic material was extracted into dichloromethane (4×50 ml). The combined organic layers was washed with brine, dried overmagnesium sulfate, and evaporated to a yellow gum. The crude product was purified by column chromatography over silica gel 60, using 20% of diethyl ether in hexane as the eluent to afford 0.15 g (40%) of 4-benzoyl-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine as a yellow solid. MS(SP): m/z 379 (M+). 1H--NMR (CDCl3, 200 MHz) δ: 1.47 (t, 3 H); 3.21 (q, 2 H); 3.89 (s, 3 H); 7.08 (d, 2 H); 7.46-7.60 (m,3 H); 7.69 (d, 2 H); 7.81-7.98 (m, 5 H); 8.39 (dd, 1 H).

Provenance & Evidence