Methyl iodide → 6-Bromo-1-methyl-1H-indazole

HRID 2112563

反応式

HRID 2112563 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I>C1COCC1>[CH3:13][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[CH:6]=[N:7]1.[CH3:13][N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[C:2]([Br:1])[CH:3]=[CH:4]2)=[N:8]1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178424716-Bromo-1H-indazole

生成物 2

HCID 225586246-bromo-2-methyl-2H-indazole収率 43%HCID 225586756-Bromo-1-methyl-1H-indazole収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 6-bromoindazole (402A) (5.0 g, 25.4 mmol) in THF (50 mL) was added sodium hydride (95%, 672 mg, 26.6 mmol) with ice bath cooling. The mixture was stirred for 30 minutes. Methyl iodide (6.36 mL, 102 mmol) was added at room temperature. The reaction mixture was quenched with ammonium chloride solution and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate and concentrated. Purification by column chromatography (SiO2, ethyl acetate/hexane gradient) afforded 1-methyl-6-bromoindazole (402B) (2.71 g, 51%) as a yellow oil and 2-methyl-6-bromoindazole (402C) (2.28 g, 43%) as a yellow crystalline solid.

後処理

  1. temperaturecooling
  2. customThe reaction mixture was quenched with ammonium chloride solution
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by column chromatography (SiO2, ethyl acetate/hexane gradient)

出典と根拠

ORDレコード
ord-588c98c774694becb0aeae6eb415fe31
出典データセット
uspto-grants-2009_04
特許番号
US07524842B2

関連ノート

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