Dimethylformamide → 8-[(2,5-difluorobenzyl)oxy]-N-[(1R)-2-hydroxy-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

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A mixture of 8.5 mg of N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxamide, 5.6 mg of α-bromo-2,5-difluorotoluene, 5.0 mg of potassium carbonate, and 700 μl of DMF was stirred at 30° C. for 28 hours. To the reaction mixture were added 1 ml of water, 0.5 ml of saturated brine, and 4 ml of chloroform to carry out a layer separation operation. The organic layer was concentrated under reduced pressure, and to the residue were added 300 μl of THF and 300 μl of 1 M hydrochloric acid, followed by stirring at room temperature for 6 hours. To the reaction mixture were added 300 μl of a 1 M aqueous sodium hydroxide solution and 100 of saturated aqueous sodium bicarbonate, followed by extraction with 3 ml of chloroform. The solvent was evaporated under reduced pressure and the obtained residue was purified by preparative HPLC to obtain 6.3 mg of 8-[(2,5-difluorobenzyl)oxy]-N-[(1R)-2-hydroxy-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

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