2-Aminothiazole → HCID 57433635, compound

Participants

Reaction Steps

To a mixture of 2-aminothiazole (0.976 g, 9.74 mmol) and 2-bromo-1-(4-fluoro-3-methoxy-phenyl)-ethanone (2.4 g, 9.74 mmol) was added absolute ethanol (100 ml). The reaction was allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture was reduced to half its original volume in vacuo. The remaining liquid was poured onto ice and the solution made basic by the addition of ammonium hydroxide solution (30%), until pH is 8. The mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with water (100 ml) and saturated aqueous sodium chloride solution (100 ml). The organic phase was dried with sodium sulfate, filtered and concentrated in vacuo, to give an orange solid. Purification by flash chromatography (gradient 25%-50% ethyl actetate in hexanes) afforded the title product as a pale yellow solid (1.59 g, 66%). 400 MHz 1H NMR (DMSO-d6) δ 8.26 (s, 1H), 7.95 (d, J=2.3 Hz, 1H), 7.61 (dd, J=8.6, 2.0 Hz, 1H), 7.39 (ddd, J=8.2, 4.3, 2.0 Hz, 1H); 7.28 (d, J=4.7 Hz, 1H), 7.22 (dd, J=11.3, 8.2 Hz, 1H), 3.91 (s, 3H). LCMS: 249 [M+H].

Provenance & Evidence