Methyl iodide → 5-Bromo-1-methyl-1H-indazole

HRID 241083

반응식

HRID 241083 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[C:11](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[CH:5]2

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 7619295-bromo-1H-indazole

생성물 1

HCID 225587255-Bromo-1-methyl-1H-indazole수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 5-bromo-1H-indazole (200 mg, 1.02 mmol), cesium carbonate (661 mg, 2.00 mmol), and iodomethane (156 mg, 1.10 mmol) in dimethylformamide (3 mL) was stirred at room temperature for 15 h. The mixture was partitioned between 5% lithium chloride and ethyl acetate, the aqueous layer was extracted with ethyl acetate (2×), the combined organic extracts were washed with 1 N sodium hydroxide, and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography on silica (hexanes/ethyl acetate 4:1) gave 5-bromo-1-methyl-1H-indazole (150 mg, 70% yield) as an orange solid. MS (EI) for C8H7BrN2: 212 (MH+).

후처리

  1. customThe mixture was partitioned between 5% lithium chloride and ethyl acetate
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  3. washthe combined organic extracts were washed with 1 N sodium hydroxide, and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-16eb5aa2b9ae4a53ac49ff40dc23ac45
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648066B2

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