Sodium Hydroxide → 5-Iodo-6-(2,2,2-trifluoroethoxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)nicotinamide

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Reaction Steps

5-Iodo-6-(2,2,2-trifluoroethoxy)nicotinic acid (Example 1a, 1 g, 2.88 mmol) was dissolved in DMF (10 mL). C-(3-trifluoromethyl-1,2,4-oxadiazol-5-yl)-methylamine hydrochloride (616 mg, 3.03 mmol), TBTU (981 mg, 3.05 mmol) and N,N-diisopropylethylamine (1.86 g, 2.45 ml, 14.4 mmol) were added. The reaction mixture was stirred overnight, poured into 75 mL 1 M NaOH solution and extracted with i-propyl acetate (2×200 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give a brown oil. The crude material was purified by flash chromatography (silica gel, 50 g, 25% i-propyl acetate in n-heptane) to give the title compound (1.2 g, 84%) as light yellow solid; MS (ESI) 497.0 (M+H)+.

Provenance & Evidence