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

HRID 706538ノート

反応式

HRID 706538 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].C(O)C.[Cl-].[NH4+]>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

6

反応物 3

HCID 702EthanolHCID 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 56%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

A flask equipped with an overhead stirrer and condenser was charged with 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (25 g, 0.081 mol) and 150 mL of ethanol, followed by 45 g (0.805 mol) of iron powder. An equal amount of saturated ammonium chloride solution was added and the mixture was brought to 80° C. After 5 hours of heating, the mixture was allowed to cool to ambient temperature, diluted with water (500 mL) and filtered through GF/F filter paper multiple times to remove the iron and iron salts. The filtrate was extracted with EtOAc, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (1:1 ethyl acetate/hexane to 100% ethyl acetate) afforded 12.6 g (56%) of 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine.

後処理

  1. customA flask equipped with an overhead stirrer and condenser
  2. customwas brought to 80° C
  3. temperatureAfter 5 hours of heating
  4. filtrationfiltered through GF/F
  5. filtrationfilter paper multiple times
  6. customto remove the iron and iron salts
  7. extractionThe filtrate was extracted with EtOAc
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f4cbe4d030be44a0959f28bc7568a39f
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…