Hydrochloric Acid → HCID 136059247, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 mg (0.28 mmol) of 4-(4-cyanophenyl)-6-(2-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in 5 ml of anhydrous DMF are added 84 mg (1.12 mmol) of sodium azide and 305 μL (366 mg, 1.12 mmol) of tributyltin chloride. The mixture is heated to 130° C. under nitrogen for 8 h. Then 19 mg (0.28 mmol) of sodium azide and 77 μL (92 mg, 0.28 mmol) of tributyltin chloride are added, and the mixture is again heated to 130° C. for 48 h. After return to room temperature, the mixture is poured onto a water/ice mixture and acidified with a 6N HCl solution. The aqueous phase is extracted once with dichloromethane and twice with chloroform. The organic phase is washed with sodium chloride saturated solution, dried over sodium sulfate, filtered, and concentrated. The solid obtained is then purified by chromatography on silica (methanol gradient in dichloromethane: 15 to 25%) to give 0.032 g (29%) of 4-(4-(2H-tetrazole-5-yl)phenyl)-6-(2-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of beige crystals.

Provenance & Evidence