Cesium carbonate → HCID 67986827, compound

Participants

Reaction Steps

A suspension of 4-(4-fluorophenethyl)piperazin-2-one (66.6 mg, 0.300 mmol), tert-butyl 7-bromo-1,1,5-trimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (120 mg, 0.300 mmol), CuI (114 mg, 0.600 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (95.0 μL, 0.600 mmol) and Cs2CO3 (195 mg, 0.600 mmol) in dioxane (5.00 mL) was degassed under reduced pressure for 5 min. The suspension was put under N2 and stirred at refluxing temperature for 24 h. The suspension was cooled, 9:0.9:0.1 CH2Cl2/MeOH/NH4OH was added, and the resulting suspension was stirred at 25° C. for 20 min. The suspension was passed through a plug of silica gel, and the filtrate was washed with brine (3×). The resulting solution was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 50:50) afforded the title compound (106 mg, 66%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 7.59 (d, J=8.5 Hz, 1H), 7.21-7.17 (m, 3H), 7.02-6.95 (m, 3H), 3.85 (t, J=5.0 Hz, 2H), 3.75 (t, J=5.0 Hz, 2H), 3.60 (s, 3H), 3.43 (s, 2H), 2.91-2.88 (m, 2H), 2.86-2.82 (m, 2H), 2.78-2.70 (m, 4H), 1.85 (s, 6H), 1.55-1.53 (m, 9H).

Provenance & Evidence