Ammonium Chloride → 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine

HRID 706623노트

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HRID 706623 반응식
[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[C:14](=[C:15]([N+:20]([O-])=O)[CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[NH4+]>CCO.O.[Fe]>[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([NH2:20])[C:14]=3[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 679762021-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole

생성물 1

HCID 679746421-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine수율 57%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (1.51 g, 4.87 mmol) in EtOH/H2O (40 mL/10 mL) was added iron (5.43 g, 97.3 mmol) and ammonium chloride (0.260 g, 4.87 mmol). The reaction mixture was heated to reflux for three hours, then cooled to 60° C. and filtered through a pad of Celite®. The filter cake was washed with EtOH/Et3N (20:1, 200 mL) and MeOH/DCM (1:1, 100 mL). The filtrate was concentrated, and the residue was dissolved in EtOAc (200 mL). The ethyl acetate was washed with NaHCO3, dried (Na2SO4), filtered and concentrated to give the desired product (57%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for three hours
  3. filtrationfiltered through a pad of Celite®
  4. washThe filter cake was washed with EtOH/Et3N (20:1, 200 mL) and MeOH/DCM (1:1, 100 mL)
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in EtOAc (200 mL)
  7. washThe ethyl acetate was washed with NaHCO3
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-76817e01fd444095aebeb226376410a5
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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