Methyl iodide → HCID 58267997、化合物

HRID 1615976ノート

反応式

HRID 1615976 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 58267997HCID 58267997、化合物収率 36.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8a04f0935a4d4690a4743577c643500c
出典データセット
uspto-grants-2014_07
特許番号
US08765743B2

反応ノート

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