Water → N,N-diethyl-3-iodo-2-isopropylimidazo[1,2-a]pyridine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Isopropylimidazo[1,2-a]pyridine-7-carboxylic acid (3.00 g, 14.7 mmol) obtained in step 2 was dissolved in DMF (15 mL), and the solution was stirred at 60° C. for 2 hours after adding EDC.HCl (4.20 g, 22.0 mmol), HOBt.H2O (3.00 g, 22.0 mmol), and diethylamine (2.70 mL, 29.4 mmol). The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with a saturated ammonium chloride aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was dissolved in DMF (20 mL), and stirred under light shielding at room temperature for 1 hour after adding N-iodosuccinimide (4.20 g, 18.5 mmol). The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was slurried with heptane. The resulting crystals were collected by filteration, and dried to give N,N-diethyl-3-iodo-2-isopropylimidazo[1,2-a]pyridine-7-carboxamide (6.40 g, yield 99%).

Provenance & Evidence