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

HRID 1615984
ノート
印刷プレビュー

反応式

HRID 1615984 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 582557716-Bromo-1-methyl-1h-indazol-4-amine収率 15%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a1a9f4dd1b714b83b443f4d75b7fa89a
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765743B2

反応ノート

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