Potassium Carbonate → 3-iodo-1-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole

HRID 79377노트

반응식

HRID 79377 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH2:7]O)=[N:3]1.S(Cl)(Cl)=O.[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[NH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CN(C=O)C>[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[N:16]([CH2:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)[N:15]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 12845046(1-methyl-1H-pyrazol-3-yl)methanolHCID 178526562HCID 178526562, 화합물

생성물 1

HCID 672615133-iodo-1-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole수율 74.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To (1-methyl-1H-pyrazol-3-yl)methanol (2.01 g, 17.93 mmol) in DCM (80 mL) at 0° C. was cautiously added thionyl chloride (10.43 mL, 143.4 mmol). The cold bath was removed and the reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The residual yellow solid was diluted with DMF (30 mL). 3-Iodo-4-nitro-1H-indazole (5.181 g, 17.93 mmol) and K2CO3 (7.432 g, 53.78 mmol) were added to the DMF solution. The reaction mixture was stirred for 20 hours, and concentrated under reduced pressure to remove most of the DMF. The residue was diluted with DCM (100 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/Hexane 1:3) to provide the product (5.11 g).

후처리

  1. customat 0° C.
  2. customThe cold bath was removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe residual yellow solid was diluted with DMF (30 mL)
  5. stirringThe reaction mixture was stirred for 20 hours
  6. concentrationconcentrated under reduced pressure
  7. customto remove most of the DMF
  8. additionThe residue was diluted with DCM (100 mL)
  9. washwashed with H2O
  10. dry with materialThe organic phase was dried (Na2SO4)
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (EtOAc/Hexane 1:3)

출처 및 근거

ORD 기록
ord-633e65df7b164fa2b174d505f013a6e6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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