Potassium Carbonate → HCID 59004597, compound

Participants

Reaction Conditions

Reaction Steps

Compound 3 (165 mg, 0.654 mmol), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (132.4 mg, 0.719 mmol), and powdered potassium carbonate (271.2 mg, 1.962 mmol) were placed in an argon-purged flask. DMF (5 mL, Aldrich sure seal™) was added and the mixture heated to 65° C. in an oil bath for 20 hours. The solution was cooled to room temperature and diluted with water (10 mL) and ethyl acetate (25 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×25 mL). The organic extracts were combined, washed with brine (2×10 mL) and dried over magnesium sulfate. The sample was filtered, concentrated, and the resultant crude product purified using dry silica gel column chromatography eluting with 15-20 mL portions of solvent system (2M NH3 in methanol:CH2Cl2, 5:95) to afford a yellow solid 4 (152 mg, 63.9%); 1H NMR (CDCl3) δ 8.50 (d, 1H, J=2.2 Hz), 8.07 (dd, 1H, J=2.2, 9.0 Hz), 7.36-7.17 (m, 6H), 6.44 (s, 1H), 4.16 (d, 2H, J=3.0 Hz), 4.10-3.97 (m, 2H), 3.06 (t, 1H, J=7.1 Hz), 2.21 (s, 3H), 2.15-2.00 (2×m, 2H), 1.97-1.55 (m, 5H), 1.53-1.40 (m, 1H); ESI-MS (m/z, %): 364 (M+1, 100%).

Provenance & Evidence