Sodium hydride → Ethyl 6-{(E)-2-[2-(cyclopentyloxy)-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-(cyclopentyloxy)-3-methoxybenzaldehyde (1.318 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 (239 mg, 5.984 mmol) in anhydrous DMSO (20 mL) to give 1.610 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40 (t, J=6.9 Hz, 3H), 1.54-1.65 (m, 4H), 1.78-1.85 (m, 4H), 3.81 (s, 3H), 4.39 (q, J=7.2 Hz, 2H), 4.83-4.86 (m, 1H), 6.99-7.02 (m, 1H), 7.09 (t, J=8.1 Hz, 1H), 7.21-7.25 (m, 1H), 7.46 (d, J=4.5 Hz, 1H), 7.67 (d, J=16.2 Hz, 1H), 7.88 (d, J=16.2 Hz, 1H), 8.12 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 413.27 (M+H)+.

Provenance & Evidence