Formaldehyde → 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine

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Reaction Steps

Sodium hydride (120 mg, 2.9 mmol) was added slowly to isopropyl alcohol (15 mL) at 0° C. Once the evolution of hydrogen ceased 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine hydrochloride (200 mg, 0.58 mmol) and paraformaldehyde (147 mg, 1.64 mmol) added. The resulting mixture was stirred at room temperature for 5 h and hydrolyzed with ice-cooled water and extracted with ethyl acetate. The organic extracts were washed with water, then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine (269 mg). The product was carried forward without further purification. 1H NMR (CDCl3): 8.38 (d, 1H), 7.44 (m, 1H), 7.35 (m, 1H), 7.00 (s, 1H), 6.70 (m, 1H), 4.80 (d, 2H), 3.90 (m, 1H), 1.22 ppm (d, 6H).

Provenance & Evidence