Sodium hydride → Ethyl 2-{(E)-2-[2-(cyclopentyloxy)-3-(difluoromethoxy)phenyl]vinyl}imidazo [1,2-a]pyridine-3-carboxylate

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Reaction Steps

Prepared by the reaction of 2-(cyclopentyloxy)-3-(difluoromethoxy)benzaldehyde (3.595 g, 14.040 mmol) with 3-ethyloxycarbonylimidazo[1,2-a]pyridine-2-yl-methyl(triphenyl)phosphonium bromide (7.0 g, 12.763 mmol) in the presence of NaH (0.561 g, 23.375 mmol) in anhydrous DMSO (15 mL) to afford 4.325 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.44 (t, J=6.9 Hz, 3H), 1.55-1.61 (m, 2H), 1.67-1.75 (m, 2H), 1.84-1.93 (m, 4H), 4.40-4.50 (m, 2H), 4.72-4.78 (m, 1H), 7.20 (t, J=74.7 Hz, 1H), 7.22-7.30 (m, 3H), 7.55-7.65 (m, 2H), 7.75 (d, J=8.7 Hz, 1H), 7.91 (d, J=16.8 Hz, 1H), 8.05 (d, J=16.2 Hz, 1H), 8.24 (d, J=5.1 Hz, 1H); APCI-MS (m/z) 443.28 (M)+.

Provenance & Evidence