Methyl iodide → 3-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridine

HRID 246565

반응식

HRID 246565 반응식
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH3:11]C(C)([O-])C.[K+].IC>C1COCC1.O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[N:3]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178506575HCID 178506575, 화합물

생성물 1

HCID 534706403-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridine수율 31%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 3-iodo-1H-pyrazolo[3,4-b]pyridine (3.5 g, 14.3 mmol) in THF (70 mL) at 0° C. was added potassium tert-butoxide (1.92 g, 17.1 mmol) and the reaction mixture stirred at 0° C. for 1 h. Iodomethane (2.43 g, 1.07 mL, 17.1 mmol) was added drop-wise, then the mixture was warmed to rt. After 6 h the mixture was diluted with water, extracted with dichloromethane, then the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, 20-60% ethyl acetate in hexanes) gave 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine (1.14 g, 4.4 mmol, 31%) as an off-white solid. MS (M+H)+=260.

후처리

  1. temperaturethe mixture was warmed to rt
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (silica, 20-60% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-750f9ba1df90465aaebfddd99af7669b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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