Cesium carbonate → 2-Phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one

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A solution of 5-iodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole (0.316 g, 0.923 mmol) in N-methylpyrrolidone (NMP) (2.7 mL) was added to 2-phenyl-5H-furo[3,2-c]pyridine-4-one (0.232 g, 1.10 mmol), Cs2CO3 (0.601 g, 1.84 mmol), trans-1,2-diaminocyclohexane (21.2 mL, 0.184 mmol) and CuI (0.210 g, 1.10 mmol) and deoxygenated with argon for 30 minutes. After stirring at 110° C. for 48 hours, the reaction mixture was cooled and diluted with MeOH (3 mL) and a solution of 7:1 MeOH/NH4OH (3 mL) and filtered through Celite. The filtrate was concentrated and then suspended with CH2Cl2 (20 mL) and water (20 mL) and extracted with CH2Cl2 (4×50 mL). The combined organics were dried (Na2SO4) and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) yielded the title compound (29.6 mg, 7%) as a brown solid: 1H NMR (500 MHz, CDCl3) δ 8.05 (s, 1H), 7.80 (d, J=7.5 Hz, 2H), 7.73 (d, J=2.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.47-7.42 (m, 3H), 7.37-7.33 (m, 3H), 6.68 (d, J=7.5 Hz, 1H), 4.60 (t, J=7.0 Hz, 2H), 3.06 (br m, 2H), 2.62 (br m, 4H), 1.81 (br m, 4H); ESI MS m/z 425 [M+H]+; HPLC (Method A) 96.4% (AUC), tR=15.0 mm.

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