Potassium Carbonate → 3-Bromo-1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-4-nitro-1H-indazole

HRID 79386

반응식

HRID 79386 반응식
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.Cl.Cl[CH2:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:16][C:17]2[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67261340HCID 67261340, 화합물HCID 178526560HCID 178526560, 화합물

생성물 1

HCID 672611563-Bromo-1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-4-nitro-1H-indazole수율 75.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 3-bromo-4-nitro-1H-indazole (Preparation B; 8.51 g, 35.2 mmol) in DMF (60 mL) was added 3-(chloromethyl)-1-ethyl-1H-pyrazole hydrochloride (6.37 g, 35.2 mmol) and K2CO3 (14.6 g, 106 mmol). The reaction mixture was stirred for 16 hours. Most of DMF was removed under reduced pressure. The remaining residue was diluted with EtOAc (300 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/hexanes 1:5) to provide the product (9.26 g).

후처리

  1. customMost of DMF was removed under reduced pressure
  2. additionThe remaining residue was diluted with EtOAc (300 mL)
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (EtOAc/hexanes 1:5)

출처 및 근거

ORD 기록
ord-246425ffe982440fb14903c05f394427
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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