Sodium Azide → HCID 59577514, compound

Participants

Reaction Steps

To a solution of 2-(3-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine (2.7 g, 8.5 mmol) in DMF (42 mL) at 0° C. was added sodium azide (0.61 g, 9.3 mmol). The mixture was stirred at (rt, 3 h), partitioned between ethyl acetate and brine, dried, filtered and concentrated. Upon addition of ethyl acetate and hexanes, precipitate was formed and filtered. Concentration and purification by silica gel flash chromatography using ethyl acetate/hexanes provided a solid that was combined with the previously filtered precipitate to provide the title compound (1.8 g, 65%). MS (ESI): mass calcd. for C15H9N5O2S, 323.05; m/z found, 324.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.09-7.95 (m, 1H), 7.74-7.64 (m, 3H), 7.36 (dd, J=8.5, 2.1, 1H), 7.22 (dd, J=7.9, 4.8, 1H), 4.50 (s, 2H).

Provenance & Evidence