Methyl iodide → 5-Bromo-4-methoxy-1-methyl-1H-indazole

HRID 1056982노트

반응식

HRID 1056982 반응식
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[H-].[Na+].[CH3:15]I>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:15])[N:6]=[CH:5]2

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 231345645-bromo-4-methoxy-1H-indazole

생성물 1

HCID 847023345-Bromo-4-methoxy-1-methyl-1H-indazole수율 66%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

A solution of 5-bromo-4-methoxy-1H-indazole (0.125 g, 0.550 mmol) in N,N-dimethylformamide (2.20 mL) was treated with sodium hydride (0.0166 g, 0.659 mmol) at 20° C. and then stirred at 20° C. for 30 min. The resultant reaction mixture was treated with methyl iodide (0.0410 mL, 0.658 mmol) and stirred at 20° C. for 1 h. The reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 100% EtOAc) gave the desired product (87 mg, 66%) as a white solid. LCMS calculated for C9H10BrN2O (M+H)+: m/z=241.0, 243.0. found: 240.9, 242.9.

후처리

  1. customThe resultant reaction mixture
  2. stirringstirred at 20° C. for 1 h
  3. customLayers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customPurification by flash column chromatography (100% hexanes to 100% EtOAc)

출처 및 근거

ORD 기록
ord-4053e82448a041d39a3fc4895374e4b1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399640B2

반응 노트

불러오는 중…