Potassium Carbonate → 5-[1-(2-Methanesulfonylethyl)-piperidin-4-yloxy]-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Participants

Reaction Steps

To a solution of 9-benzenesulfonyl-5-[1-(2-methanesulfonylethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (6138 mg, 0.26 mmol) in methanol (10 mL) was added potassium carbonate (353 mg, 2.6 mmol) and the resultant suspension was heated to 40° C. for 3 hours. After this time, the reaction mixture was loaded directly onto a 5 g SPE NH2 cartridge, which was eluted with 1:1 methanol: dichloromethane. The appropriate fractions were concentrated in-vacuo and the resultant residue purified by flash chromatography (silica, 25 g column, Si-SPE, 0-5% 2N NH3 in methanol in dichloromethane) to afford the title compound as a pale yellow solid (49 mg, 47%). 1H NMR (400 MHz, DMSO-d6): 12.96 (s, 1H), 8.79 (s, 1H), 8.71 (dd, J=4.8, 1.6 Hz, 1H), 8.59 (dd, J=7.9, 1.6 Hz, 1H), 7.47 (dd, J=7.9, 4.8 Hz, 1H), 4.87-4.57 (m, 1H), 3.28-3.26 (m, 2H obscured by solvent peak), 3.04 (s, 3H), 3.02-2.77 (m, 2H), 2.73 (t, J=6.8 Hz, 2H), 2.20 (t, J=10.8 Hz, 2H), 2.21-1.97 (m, 2H), 1.96-1.89 (m, 2H).

Provenance & Evidence