Sodium hydride → Ethyl 6-{(E)-2-[2-(cyclopentyloxy)-3-(difluoromethoxy)phenyl]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, step-4, by the reaction of 2-(cyclopentyloxy)-3-(difluoromethoxy)benzaldehyde (3.26 g, 12.766 mmol) with 5-ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide (6.40 g, 11.605 mmol) in the presence of sodium hydride (510 mg, 12.766 mmol) in anhydrous DMSO (20 mL) to give 4.20 g the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40 (t, J=6.9 Hz, 3H), 1.54-1.60 (m, 2H), 1.65-1.72 (m, 2H), 1.80-1.86 (m, 4H), 4.35-4.44 (m, 2H), 4.70-4.78 (m, 1H), 7.10-7.16 (m, 2H), 7.18 (t, J=73.2 Hz, 1H), 7.40-7.46 (m, 1H), 7.54-7.60 (m, 1H), 7.74 (d, J=15.9 Hz, 1H), 7.85 (d, J=16.2 Hz, 1H), 8.10-8.16 (m, 1H); ESI-MS (m/z) 449.10 (M+H)+.

Provenance & Evidence