Ethanol → 1-benzyl-3-cyclopropyl-1H-indazol-4-amine

HRID 79264노트

반응식

HRID 79264 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH:20]2[CH2:22][CH2:21]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([CH:20]2[CH2:21][CH2:22]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 672600391-benzyl-3-cyclopropyl-4-nitro-1H-indazole

생성물 1

HCID 672597331-benzyl-3-cyclopropyl-1H-indazol-4-amine수율 66.7%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

To a reaction flask was added 1-benzyl-3-cyclopropyl-4-nitro-1H-indazole (60.0 mg, 0.205 mmol), iron powder (114 mg, 2.05 mmol) and ammonium chloride (10.9 mg, 0.205 mmol). Ethanol (0.8 mL) and water (0.2 mL) were added and the mixture was heated at 85° C. with stirring for 60 minutes. The solvent was removed under reduced pressure. Ethyl acetate (0.8 mL) and triethylamine (0.2 mL) was added and the mixture was heated at 60° C. for 10 minutes. The mixture was filtered through glass fiber filter paper, washing with methanol and ethyl acetate. The filtrate was concentrated under reduced pressure. The material was purified by preparative chromatography, eluting with 3% methanol in dichloromethane, containing 0.5% ammonium hydroxide solution to give 1-benzyl-3-cyclopropyl-1H-indazol-4-amine (36 mg).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionEthyl acetate (0.8 mL) and triethylamine (0.2 mL) was added
  3. temperaturethe mixture was heated at 60° C. for 10 minutes
  4. filtrationThe mixture was filtered through glass fiber
  5. filtrationfilter paper
  6. washwashing with methanol and ethyl acetate
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe material was purified by preparative chromatography
  9. washeluting with 3% methanol in dichloromethane
  10. additioncontaining 0.5% ammonium hydroxide solution

출처 및 근거

ORD 기록
ord-059cd12138994b049a25a5e13fbb0f92
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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