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Methyl iodide → 6-Bromo-1-methyl-1h-indazol-4-amine

HRID 1615984
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HRID 1615984 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.[H-].[Na+].[CH3:14]I>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][N:8]([CH3:14])[C:9]=2[CH:10]=1
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 247280636-Bromo-1H-indazol-4-amine

생성물 1

HCID 582557716-Bromo-1-methyl-1h-indazol-4-amine수율 15%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

6-Bromo-1H-indazol-4-amine (available from Sinova, 300 mg, 1.42 mmol) was dissolved in THF (7.5 ml) and the mixture cooled to 0° C. Sodium hydride (62 mg, 1.56 mmol) was then slowly added. The mixture was stirred for 15 minutes, then methyl iodide (221 mg, 1.56 mmol) was added and stirring continued at 0° C. for 3 h. The reaction mixture was quenched by careful addition of methanol (2 ml), then water (10 ml), then extracted into ethyl acetate and the organic layer was concentrated in vacuo. The residue was purified by column chromatography on silica eluting with a gradient of 0-50% ethyl acetate in cyclohexane. Fractions containing desired product were combined and concentrated in vacuo to afford the title compound (48 mg).

후처리

  1. stirringstirring
  2. waitcontinued at 0° C. for 3 h
  3. customThe reaction mixture was quenched by careful addition of methanol (2 ml)
  4. extractionwater (10 ml), then extracted into ethyl acetate
  5. concentrationthe organic layer was concentrated in vacuo
  6. customThe residue was purified by column chromatography on silica eluting with a gradient of 0-50% ethyl acetate in cyclohexane
  7. additionFractions containing desired product
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a1a9f4dd1b714b83b443f4d75b7fa89a
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765743B2

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