HCID 69360103, 화합물 → Methyl 4-amino-1-ethyl-1H-indazole-6-carboxylate

HRID 852596노트

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HRID 852596 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([N+:16]([O-])=O)[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[N:4]1)[CH3:2]>CO.O.[Pd]>[NH2:16][C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[C:11]2[C:6]=1[CH:5]=[N:4][N:3]2[CH2:1][CH3:2]

참가 물질

5

반응물 1

HCID 69360103HCID 69360103, 화합물

생성물 1

HCID 45095359Methyl 4-amino-1-ethyl-1H-indazole-6-carboxylate수율 80.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a solution of methyl 1-ethyl-4-nitro-1H-indazole-6-carboxylate (D198) (2.2 g, 8.8 mmol, 1 equiv) in MeOH (100 ml) and H2O (10 ml) was added 10% palladium on charcoal (50% wet, 700 mg, 16% w/w) and the resulting mixture was stirred at 60° C. for 30 min then cooled to room temperature. The catalyst was removed by filtration through a pad of celite and most of the solvent removed in vacuo. The residue was partitioned between AcOEt and a saturated aqueous NaHCO3 solution and the two layers were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was triturated with iso-hexane to give methyl 4-amino-1-ethyl-1H-indazole-6-carboxylate (D199) (1.55 g, 80%) which was used in the next step without further purification. [M+H]+=220.1, RT=3.31 min.

후처리

  1. temperaturethen cooled to room temperature
  2. customThe catalyst was removed by filtration through a pad of celite and most of the solvent
  3. customremoved in vacuo
  4. customThe residue was partitioned between AcOEt
  5. customa saturated aqueous NaHCO3 solution and the two layers were separated
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with iso-hexane

출처 및 근거

ORD 기록
ord-9f166f93506d4b30aeabb22d70a9ffc0
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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