Potassium Hydroxide → HCID 89526503, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine-6-carboxylic acid (1.95 g, 4.03 mmol) in 1,4-dioxane (19.50 mL) and diphenylphosphoryl azide (DPPA) (1.047 mL, 4.83 mmol), TEA (0.842 mL, 6.04 mmol) in 10 mL of 1,4-dioxane was added dropwise over 5 min. The clear solution was heated to 80° C. for 2 h and a yellow clear solution was obtained. A solution of 1N KOH (20.13 mL, 20.13 mmol) was added at the same temperature. The reaction mixture was heated to 80° C. overnight. After cooling down to room temperature, the reaction mixture was extracted with EtOAc. The combined organic layer was washed with brine and then dried (Na2SO4). After filtration and removal of solvent, the residue was purified by column chromatography on silica gel 50 g, eluting with 50% EtOAc in hexane to give the product 9a as an off white solid (0.61 g, 1.34 mmol, 33%). MS ESI calc'd. for C25H20BrN4 [M+H]+455, found 455.

Provenance & Evidence