반응 #1703170

ord-44e6058fb35b40f39c6b435c0fc2c8c9

반응 조건

온도
20°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.WAITthen left
  2. 2
    workup.WAITto stand for 3 days
  3. 3
    workup.STIRRINGstirred at 20° C. for 20 h
  4. 4
    여과The solution was filtered through a filter tube
  5. 5
    세척the residue washed with methanol (5 ml)
  6. 6
    기타the combined filtrates were evaporated to dryness
  7. 7
    기타to give a yellow solid
  8. 8
    workup.DISSOLUTIONthe solid dissolved
  9. 9
    기타The organic phase was separated
  10. 10
    건조dried with sodium sulphate
  11. 11
    여과filtered
  12. 12
    기타then evaporated
  13. 13
    기타to give a pale yellow solid
  14. 14
    workup.DISSOLUTIONsome white solid did not dissolve
  15. 15
    기타to give a yellow solid which
  16. 16
    기타DMSO (1 ml) and purified by mass
  17. 17
    기타The residue was azeotroped with methanol (5 ml)

실험 절차

A mixture of 6-bromo-3-fluoro-4-nitro-1H-indazole and 6-bromo-4-nitro-1H-indazole (3:2) (187 mg) was dissolved in methanol (6 ml) and water (1.2 ml) and treated with sodium dithionate (519 mg). The solution was stirred for 2 h at 20° C. then left to stand for 3 days. This solution was then treated with sodium dithionite (438 mg) and stirred at 20° C. for 20 h. The solution was filtered through a filter tube, the residue washed with methanol (5 ml) then the combined filtrates were evaporated to dryness to give a yellow solid. This was treated with ethyl acetate (10 ml) and water (10 ml) and the solid dissolved. The organic phase was separated, dried with sodium sulphate, filtered then evaporated to give a pale yellow solid. This solid was treated with DCM (5 ml), methanol (5 ml) and ethyl acetate (10 ml), but some white solid did not dissolve. The supernatant was pipetted off, then blown to dryness to give a yellow solid which was dissolved in 1:1 methanol:DMSO (1 ml) and purified by mass directed preparative HPLC (Method A). The residue was azeotroped with methanol (5 ml) to give the title compound (19 mg) as a white solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08765743B2uspto-grants-2014_07