Methyl iodide → HCID 58267997, 화합물

HRID 1615976노트

반응식

HRID 1615976 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[H-].[Na+].I[CH3:17]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:17])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 247280596-bromo-4-nitro-1H-indazole

생성물 1

HCID 58267997HCID 58267997, 화합물수율 36.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

6-Bromo-4-nitro-1H-indazole (available from Sinova, 1.05 g, 4.13 mmol) was dissolved in THF (20 ml) and cooled to 0° C. under nitrogen. 60% Sodium hydride in mineral oil (191 mg, 7.57 mmol) was added portion-wise allowing the evolution of gas to subside before adding the next portion. This was left under nitrogen, stirring at 0° C. for 15 mins. Iodomethane (0.298 ml, 4.78 mmol) in THF (5 ml) was added dropwise to the reaction, washing through with further THF (5 ml). The reaction was then allowed to warm to room temperature. The reaction was stirred for 5 h then partitioned between ethyl acetate and water, washing the water with ethyl acetate (x3). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was purified by silica chromatography using a gradient of 0-25% ethyl acetate in cyclohexane, to give the title compound (388 mg).

후처리

  1. additionbefore adding the next portion
  2. waitThis was left under nitrogen
  3. washwashing through with further THF (5 ml)
  4. temperatureto warm to room temperature
  5. stirringThe reaction was stirred for 5 h
  6. customthen partitioned between ethyl acetate and water
  7. washwashing the water with ethyl acetate (x3)
  8. washThe combined organics were washed with brine
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated to dryness
  12. customThe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-8a04f0935a4d4690a4743577c643500c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765743B2

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