Cesium carbonate → HCID 118272274, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (Intermediate 1C; 5.0 g, 9.58 mmol), acetylacetone (0.979 mL, 9.58 mmol), cupric acetylacetonate (0.251 g, 0.958 mmol), and cesium carbonate (6.24 g, 19.17 mmol) in DMF (25.2 mL) were charged in a sealed vessel. The system was degassed and ammonium hydroxide (13.33 mL, 96 mmol) was added. The reaction was heated at 60° C. for 16 h. The reaction was then poured into a solution of 10% NH4OH aq. (150 mL), brine (50 mL), and EtOAc (75 mL). The layers were separated and the aqueous phase was extracted with EtOAc (75 mL). The combined organic layers were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography (0-45% EtOAc/Hexanes) to afford 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine. MS ESI calc'd. for C25H19ClN4 [M+1]+ 411. found 411.

Provenance & Evidence