反应详情

Sodium periodate (3.83 g, 17.9 mmol) was added to a stirred solution of (11) (1.94 g, 5.90 mmol) in 3:1 acetone-water (55 mL). The mixture was heated briefly to obtain homogeneity, and a 2.5% solution of osmium tetroxide in t-butanol (0.4 mL) was added. After 20 h, the mixture was diluted with water (50 mL) and saturated sodium thiosulfate (50 mL), and extracted with ethyl acetate. The combined extracts were concentrated under vacuum, and the residue was stirred in dichloromethane (40 mL) and 4 N HCl (5 mL) for 4 h. The mixture was poured into saturated NaHCO3, extracted with dichloromethane, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed (elution with dichloromethane) to afford 0.929 g (50%) of diazaindole (12) as a white solid.

1. temperatureThe mixture was heated briefly
2. customto obtain homogeneity
3. extractionextracted with ethyl acetate
4. concentrationThe combined extracts were concentrated under vacuum
5. wait4 N HCl (5 mL) for 4 h
6. additionThe mixture was poured into saturated NaHCO3
7. extractionextracted with dichloromethane
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. customThe residue was chromatographed
11. wash(elution with dichloromethane)