Methylhydrazine → 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate

HRID 1909924ノート

反応式

HRID 1909924 の反応式
[C:1]([C:3]1[C:8](F)=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)#[N:2].[CH3:26][NH:27][NH2:28]>CCO>[NH2:2][C:1]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]3)[N:27]([CH3:26])[N:28]=1

参加物

4

反応物 2

HCID 6061MethylhydrazineHCID 668237921,1-dimethylethyl 5-(2-cyano-3-fluorophenyl)-2,3-dihydro-1H-indole-1-carboxylate

生成物 1

HCID 668240801,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a suspension of 1,1-dimethylethyl 5-(2-cyano-3-fluorophenyl)-2,3-dihydro-1H-indole-1-carboxylate (1.60 g, 4.73 mmol) in 30 mL of EtOH was added 7 mL of methylhydrazine in one portion. The mixture was heated in an oil bath at 100° C. for 24 h. LCMS showed conversion complete. The mixture was cooled and concentrated in vacuo. The residue was partitioned between DCM (60 mL) and water (30 mL). The organic was dried over Na2SO4, filtered, and concentrated in vacuo to give 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate as a cream-colored foamy solid (1.70 g).

後処理

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between DCM (60 mL) and water (30 mL)
  4. dry with materialThe organic was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-aa6d53c9cd6447e9956be7f7c08f4d36
出典データセット
uspto-grants-2013_12
特許番号
US08598156B2

反応ノート

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