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

HRID 501271

반응식

HRID 501271 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-11ee07161b1848069adbb6445ffc0db4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772263B2

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