反应详情

To a solution of 3-(3,4-dimethoxyphenyl)-1H-indazole-5-carbonitrile (190 mg, 0.68 mmol) in toluene (10 mL) was added tributyltin azide (930 μL, 3.4 mmol). The solution was heated to reflux for 12 hours when 3 N NaOH (80 mL) was added and the solution extracted with ethyl acetate (2×20 mL). The aqueous layer was then acidified with 4 N HCl to pH<1 and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (Na2SO4) and concentrated to an oil. After remaining at room temperature for 14 hours, the product crystallized from solution to recover, after filtration and drying, the title compound (115 mg, 53% yield). 1H NMR (DMSO-d6) δ 13.4 (s, 1H), 8.70 (s, 1H), 8.04 (d, 1H), 7.75 (d, 1H), 7.54 (d, 1H), 7.49 (s, 1H), 7.12 (d, 1H), 3.85 (s, 3H), 3.81 (s, 3H); ES-MS (m/z) 323 [M+1]+.

1. temperatureThe solution was heated
2. additionwas added
3. extractionthe solution extracted with ethyl acetate (2×20 mL)
4. extractionextracted with ethyl acetate (3×30 mL)
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated to an oil
7. customthe product crystallized from solution
8. customto recover
9. filtrationafter filtration
10. customdrying