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

Participants

Reaction Steps

To a solution of 9-benzenesulfonyl-5-[1-(2,2-difluoroethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (68 mg, 0.14 mmol) in methanol (5 mL) was added potassium carbonate (193 mg, 1.4 mmol) and the resultant suspension was heated to 40° C. for 4 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, 10 g column, Si-SPE, 0-4% 2N NH3 in methanol in dichloromethane) to afford the title compound as a pale yellow solid (36 mg, 73%). LCMS (Method C): RT=6.07 min, M+H+=358. 1H NMR (300 MHz, CD3OD): 8.74 (s, 1H), 8.64-8.64 (m, 2H), 7.58 (s, 1H), 7.43 (dd, J=7.9, 4.9 Hz, 1H), 5.94 (tt, J=55.8, 4.2 Hz, 1H), 4.93-4.92 (m, 1H), 3.11-2.99 (m, 2H), 2.82 (td, J=15.1, 4.3 Hz, 2H), 2.51-2.51 (m, 2H), 2.15-2.14 (m, 4H).

Provenance & Evidence