Development of a Scalable Synthesis for the Potent Kinase Inhibitor BMS-986236; 1-(5-(4-(3-Hydroxy-3-methylbutyl)-1H-1,2,3-triazol-1-yl)-4-(isopropylamino)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

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A scalable route to 1-(5-(4-(3-hydroxy-3-methylbutyl)-1 H -1,2,3-triazol-1-yl)-4-(isopropylamino)pyridin-2-yl)-1 H -pyrazolo[3,4- b ]pyridine-5-carbonitrile ( 1, BMS-986236 ) was developed by incorporating an alternate azide intermediate following safety-driven processes. The newly developed process involved mitigating safety hazards and eliminating the column chromatography purification. The issue of trace metal contamination in the final API observed in the first-generation synthesis has been overcome.