Tributyltin azide → HCID 178419934, compound

Participants

Reaction Steps

A mixture of 3-(2-naphthyl)-1H-indazole-5-carbonitrile (105 mg, 0.390 mmol), azidotributyltin (Bu3SnN3, 710 mg, 2.14 mmol, 5.49 equiv.), and 4.1 mL toluene was refluxed for 49.5 h and concentrated to an oil. The oil was stirred in 31 mL dioxane and 31 mL 6.0 N aq HCl at room temperature for 4 h. The mixture was partitioned between 6.0 N aq. NaOH and hexanes, and the layers separated. The aqueous layer was extracted with hexanes, and 2× EtOAc, and then filtered. The aqueous layer was acidified to pH ca. 4.0 with 6.0 N aq. HCl. The resulting precipitate was either collected by filtration and dried in a vacuum oven, or extracted with EtOAc, dried (Na2SO4), filtered and concentrated to afford the title compound (78.4 mg, 64.3% yield): 1H NMR (DMSO-d6) δ 13.70 (s, 1H), 8.92 (s, 1H), 8.60 (s, 1H), 8.17 (d, 1H), 8.15-8.00 (m, 3H), 7.94 (d, 1H), 7.85 (d, 1H), 7.63-7.58 (m, 2H); ES-MS (m/z) 313 [M+1]+.

Provenance & Evidence