反应详情

To a solution of 3-(2-hydroxy-ethyl)-benzofuran-6-ol (0.42 g, 2.4 mmol) in DMF (24 mL) was added Cs2CO3 (0.77 g, 2.4 mmol) and 2-chloro-thiazolo[4,5-b]pyridine hydrochloride (0.49 g, 2.4 mmol) and the reaction mixture was stirred (rt, 15 h) and then heated (50° C., 2 h). The reaction mixture was cooled (rt) and partitioned with EtOAc and brine (50 mL each). The aqueous layer was extracted with EtOAc (50 mL). The organic layer was washed with brine (50 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-100%) to provide the title compound as an amber oil (0.42 g, 57%). MS (ESI): mass calcd. for C16H12N2O3S, 312.3; m/z not found. 1H NMR (500 MHz, CDCl3): 8.56 (dd, J=4.8, 1.7, 1H), 8.02 (dd, J=8.0, 1.6, 1H), 7.61-7.57 (m, 3H), 7.30 (dd, J=8.4, 2.2, 1H), 7.21 (dd, J=8.0, 4.8, 1H), 3.95 (q, J=6.1, 2H), 2.97-2.94 (m, 2H), 1.75 (t, J=5.5, 1H).

1. temperatureheated (50° C., 2 h)
2. temperatureThe reaction mixture was cooled (rt)
3. custompartitioned with EtOAc and brine (50 mL each)
4. extractionThe aqueous layer was extracted with EtOAc (50 mL)
5. washThe organic layer was washed with brine (50 mL)
6. customdried
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting residue was purified by silica gel flash chromatography