Sodium hydride → Ethyl 6-{(E)-2-[2-(isobutoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

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Reaction Steps

This compound was prepared as described in Intermediate 1 by the reaction of 2-isobutoxy-3-methoxybenzaldehyde (1.328 g, 5.984 mmol) with 5-ethyloxycarbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide (3.0 g, 5.440 mmol) in the presence of sodium hydride (0.23 g, 5.984 mmol) in anhydrous DMSO (15 mL) to give 1.50 g of product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (d, J=6.9 Hz, 6H), 1.47 (t, J=6.9 Hz, 3H), 2.12-2.23 (m, 1H), 3.75 (d, J=6.6 Hz, 2H), 3.86 (s, 3H), 4.40-4.49 (m, 2H), 6.85 (d, J=7.8 Hz, 1H), 6.90 (d, J=4.5 Hz, 1H), 7.05 (t, J=7.8 Hz, 1H), 7.28-7.33 (m, 1H), 7.76 (d, J=16.2 Hz, 1H), 8.03 (d, J=16.2 Hz, 1H), 8.07-8.11 (m, 1H); APCI-MS (m/z) 399.09 (M−H)−.

Provenance & Evidence