Sodium Bicarbonate → 4-(6-nitro-1H-indol-3-yl)-benzonitrile

HRID 2079892

반응식

HRID 2079892 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1(S([N:28]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([N+:37]([O-:39])=[O:38])[CH:35]=3)[C:30]([C:40]3[CH:47]=[CH:46][C:43]([C:44]#[N:45])=[CH:42][CH:41]=3)=[CH:29]2)(=O)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.CC(C)=O>[N+:37]([C:34]1[CH:35]=[C:36]2[C:31]([C:30]([C:40]3[CH:41]=[CH:42][C:43]([C:44]#[N:45])=[CH:46][CH:47]=3)=[CH:29][NH:28]2)=[CH:32][CH:33]=1)([O-:39])=[O:38]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium Fluoride2회HCID 574422424-(1-benzenesulfonyl-6-nitro-1H-indol-3-yl)-benzonitrile

생성물 1

HCID 574421974-(6-nitro-1H-indol-3-yl)-benzonitrile

시약·촉매·용매 2

HCID 180Acetone용매HCID 8028Tetrahydrofuran용매3회

실험 절차

Add 100 mL of 1 M TBAF in THF to a slurry of 4-(1-benzenesulfonyl-6-nitro-1H-indol-3-yl)-benzonitrile 8 (14.3 g, 35 mmol) in 50 mL of THF. Monitor the reaction by TLC. If starting material remains add more 1 M TBAF in THF until the reaction is complete. Pour reaction mixture into 200 mL of saturated aqueous sodium bicarbonate and then extract the resulting solution 3× with EtOAc. Combine the organic extracts and wash the extracts with saturated aqueous bicarbonate, water (2×), brine. Dry the resulting organic solution over Na2SO4, filter, and then remove the organic solvent to provide a solid. Redisolve the solid in ˜400 mL of acetone with heating and then add ˜100 mL hexanes until a precipitate forms. Let the solution cool and then collect the precipitate. Concentrate the filtrates and redisolve in ˜300 mL of 50% acetone/hexanes with heating. Let the solution cool and then place in a freezer at −20° C. overnight. Collect the crystals that form. The combined yield of the title compound is 6.71 g, 25.5 mmol, 72%. LRMS (API ES−)=262.0 (M−1).

후처리

  1. customMonitor the reaction by TLC
  2. additionPour
  3. extractionextract the resulting solution 3× with EtOAc
  4. washwash the extracts with saturated aqueous bicarbonate, water (2×), brine
  5. dry with materialDry the resulting organic solution over Na2SO4
  6. filtrationfilter
  7. customremove the organic solvent
  8. customto provide a solid
  9. temperaturewith heating
  10. temperaturecool
  11. customcollect the precipitate
  12. concentrationConcentrate the filtrates
  13. temperaturewith heating
  14. temperaturecool
  15. customCollect the crystals that form

출처 및 근거

ORD 기록
ord-57336213eff141c2b05476d1b1da5eae
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

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