HCID 69360103、化合物 → Methyl 4-amino-1-ethyl-1H-indazole-6-carboxylate

HRID 852596ノート

反応式

HRID 852596 の反応式
[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]

参加物

5

反応物 1

HCID 69360103HCID 69360103、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f166f93506d4b30aeabb22d70a9ffc0
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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