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

HRID 706538노트

반응식

HRID 706538 반응식
[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]

참가 물질

6

반응물 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 679762021-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole

생성물 1

HCID 679746421-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine수율 56%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4cbe4d030be44a0959f28bc7568a39f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

반응 노트

불러오는 중…