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

HRID 706623ノート

反応式

HRID 706623 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-76817e01fd444095aebeb226376410a5
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

読み込み中…