2-(azetidin-1-yl)ethanol

Conditions: temp:88.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Azetidin-1-yl)ethanol (52 mg, 0.51 mmol) was dissolved in tert-butanol (0.3 mL) and treated with potassium tert-butoxide (51 mg, 0.45 mmol). The mixture was stirred at 88° C. for 5 minutes before adding 7-fluoro-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide in one portion. The mixture was stirred at 88° C. for 16 hours. The mixture was cooled to ambient temperature and quenched with water (2 mL) followed by vigorous stirring for 2 hours at ambient temperature. The precipitate was isolated by filtration and dried under vacuum to give a pale yellow residue which was triturated with diethyl ether 3 times to give a solid. Purification by Preparative Thin Layer Chromatography (Silica, 20×20, 0.5 mm thickness) eluting with 10% MeOH/DCM with 0.6% ammonium hydroxide gave 7-(2-(azetidin-1-yl)ethoxy)-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide as a white solid (18 mg). MS (APCI), positive scan, m/z=522.2 (M+1). The mixture was stirred at 88° C. for 16 hours The mixture was cooled to ambient temperature quenched with water (2 mL) by vigorous stirring for 2 hours at ambient temperature The precipitate was isolated by filtration dried under vacuum to give a pale yellow residue which was triturated with diethyl ether 3 times to give a solid Purification by Preparative Thin Layer Chromatography (Silica, 20×20, 0.5 mm thickness) eluting with 10% MeOH/DCM with 0.6% ammonium hydroxide