Ammonium Chloride → 7-bromo-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

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A mixture of ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (0.54 g, 2.0 mmol) and 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (0.56 g, 2.0 mmol; prepared as in Example 65, steps A1-A3) in THF (10 mL) was cooled to −13° C. using an ice/water/MeOH bath. A solution of 1.0M lithium bis(trimethylsilyl)amide (4.4 mL, 4.4 mmol) was added over 5 minutes keeping the internal temperature below −10° C. The mixture was stirred at −10° C. for 10 minutes, warmed to ambient temperature and concentrated to give an oily residue. The residue was dissolved using IPA (10 mL) and treated with a 10% aqueous ammonium chloride solution (20 mL) to give a slurry which was stirred overnight. The slurry was filtered to collect the solid which was dried under vacuum to give the product (0.89 g). MS (ES+APCI) m/z=501.0 (M+H).

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