Sodium Iodide → HCID 11858050, compound

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Reaction Steps

2-methylpyrrolidine (0.24 ml, 2.46 mmol, 1.2 eq) is added to a solution of 2-[4-(3-chloropropoxy)phenyl]-N-(cyclopropylmethyl)-4-methyl-N-propyl-1,3-oxazole-5-carboxamide i44 (0.8 g, 2 mmol, 1 eq), potassium carbonate (0.55 g, 4 mmol, 2 eq) and a catalytic quantity of sodium iodide in refluxing acetonitrile (25 ml). After stirring for 20 h at reflux, the solvent is evaporated and the residue is taken up in ethyl acetate and washed two times with an aqueous solution of sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96:3.6:0.4) affords 0.31 g of N-(cyclopropylmethyl)-4-methyl-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-N-propyl-1,3-oxazole-5-carboxamide 97.

Provenance & Evidence