Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-one

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Reaction Steps

A 2 L 3-neck round bottom flask is charged with 1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone (215 g, 0.88 mol) and dimethylformamide dimethylacetal (1.1 L). The mixture is refluxed for 5 hours and then cooled to room temperature. Solvent is removed under vacuum, and the resulting solid is filtered and washed with MTBE (methyl tert-butyl ether) to give the desired product (229.0 g) in 87% yield as light yellow solid. M.p.=187-189° C.; 300 MHz 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.72-7.64 (m, 3H), 7.46 (s, 1H), 7.13-7.10 (m, 2H), 5.19 (d, J=12.5 Hz, 1H), 3.07 (bs, 3H), 2.55 (bs, 3H). LCMS: 300 [M+H]. Calc. for C16H14FN3O2: C, 64.21; H, 4.71; N, 14.04; found. C, 64.22; H, 4.31; N, 14.10.

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