Cesium carbonate → HCID 25017297, compound

Participants

Reaction Steps

To a solution of 2-(3-chlorophenyl)-5-(1H-indazol-5-yl)furo[3,2-c]pyridin-4(5H)-one (0.365 g, 0.732 mmol) in DMSO (1.5 mL) and NMP (0.94 mL) was added (2-chloroethyl)pyrrolidine hydrochloride (0.273 g, 1.61 mmol) and Cs2CO3 (1.43 g, 4.39 mmol). The reaction mixture was stirred at ambient temperature for 18 h; then the reaction mixture was diluted with H2O (10 mL) and EtOAc (20 mL). The desired solids were collected by filtration. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) yielded the title compound (83.8 mg, 25%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.05 (s, 1H), 7.79 (t, J=2.0 Hz, 1H), 7.72 (d, J=1.5 Hz, 1H), 7.66 (d, J=7.5 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.42 (dd, J=8.5, 2.0 Hz, 1H), 7.39-7.35 (m, 2H), 7.33-7.31 (m, 1H), 7.29 (s, 1H), 6.68 (d, J=7.5 Hz, 1H), 4.58 (t, J=7.5 Hz, 2H), 3.03 (t, J=7.0 Hz, 2H), 2.60 (m, 4H), 1.80 (m, 4H); ESI MS m/z 459 [M+H]+; HPLC (Method A) >99% (AUC), tR=16.7 min.

Provenance & Evidence