3-(2-Thienyl)-5-isoxazolamine → Ethyl 6-(5-methylpyridin-3-yl)-3-(thiophen-2-yl)isoxazolo[5,4-b]pyridine-4-carboxylate

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A mixture of 1-3 (150 mg, 0.638 mmol) and 1-4 (106 mg, 0.638 mmol) in acetic acid (3 mL) was heated at reflux for 3 h. The mixture was cooled to rt and concentrated. The residue was purified by column chromatography (0-100% EtOAc in hexane) to give 1-5 as a white solid: 1H NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 8.59 (s, 1H), 8.36 (s, 1H), 8.15 (s, 1H), 7.58 (m, 1H), 7.39 (m, 1H), 7.22 (m, 1H), 4.21 (q, J=7.2 Hz, 2H), 2.48 (s, 3H), 1.07 (t, J=7.2 Hz, 3H); ESI+ MS [M+H]+ C19H16N3O3S=366.0.

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