Cesium carbonate → HCID 25017033, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole (0.349 g, 1.18 mmol) in NMP (3.3 mL) was added to 2-(4-chlorophenyl)-5H-furo[3,2-c]pyridine-4-one (0.347 g, 1.41 mmol), Cs2CO3 (0.768 g, 2.36 mmol), trans-1,2-bis(methylamino) cyclohexane (0.035 mL, 0.236 mmol) and CuI (0.269 g, 1.41 mmol) and deoxygenated with argon for 30 minutes. After stirring at 110° C. for 48 hours, the reaction mixture was cooled and diluted with CH2Cl2 (10 mL) and water (10 mL) and extracted with CH2Cl2 (4×50 mL). The organics were filtered through Celite and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) followed by preparative HPLC (Phenomenex Luna C18 (2), 250.0×50.0 mm, 10 micron, H2O with 0.05% trifluoroacetic acid (TFA) and CH3CN with 0.05% TFA) yielded the title compound (7.5 mg, 13%) as a light yellow solid: ESI MS m/z 459 [M+H]+.

Provenance & Evidence