Dimethyl Sulfoxide → 4-[2-(3-Naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-en-8-yl)-ethoxy]-1H-indole

Participants

Reaction Conditions

Reaction Steps

4-(2-Chloro-ethoxy)-1H-indole (170 mg, 0.87 mmol), 469 mg (1.74 mmol) of 3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-ene and 10 mL of DMSO are heated at 100° C. for 24 h. After cooling to 23° C., the orange reaction mixture is poured into 100 mL H2O. Extraction with CH2Cl2 (2×50 mL), combining the organic layers and washing with H2O (4×50 mL), brine (1×50 mL), drying over MgSO4, and evaporation gives an orange oil. Flash chromatography on SiO2 gel, eluting with CHCl3/MeOH (40/1 to 10/1), gives 216 mg (0.59 mmol, a 63% yield) of the title compound as an off-white solid. The corresponding oxalate salt is prepared by combining the title compound with 1 equiv. of oxalic acid in EtOH. A white solid precipitates. Recrystallization from EtOH/Et2O gives the oxalate salt of the title compound as an off-white solid. mp: 212-215° C.; MS (ES) m/z 395 (MH)+.

Provenance & Evidence