Sodium Iodide → 1-(4-Iodo-pyrazolo[3,4-b]pyridin-1-yl)ethanone

HRID 1861124노트

반응식

HRID 1861124 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[I-:11].[Na+].[C:13](Cl)(=[O:15])[CH3:14].OS([O-])=O.[Na+]>C(#N)C>[I:11][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:13](=[O:15])[CH3:14])[N:9]=[CH:10][C:3]=12

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 3100454-Chloro-1H-pyrazolo[3,4-b]pyridineHCID 23665763Sodium Bisulfite

생성물 1

HCID 218774001-(4-Iodo-pyrazolo[3,4-b]pyridin-1-yl)ethanone수율 42%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4-chloro-1H-pyrazolo[3,4-b]pyridine (820 mg, 5.30 mmol), sodium iodide (2.4 mg, 16.0 mmol), and acetyl chloride (0.8 ml) in acetonitrile (6 ml) was refluxed 8 h. The mixture was then treated with a 10% aqueous solution of NaCO3 (10 ml), and a 10% aqueous solution of NaHSO3 (10 ml), and held 10 min. The mixture was extracted with ethyl acetate (50 ml), and the organics were washed with brine (10 ml), dried over MgSO4, and evaporated under reduced pressure. Purification by silica gel chromatography gave 1-(4-iodo-pyrazolo[3,4-b]pyridin-1-yl)-ethanone as a brown solid (650 mg, 42%). 1H NMR (300 MHz, CDCl3) δ 8.39 (d, 1H, J=5.0 Hz), 8.04 (s, 1H), 7.76 (d, 1H, J=5.0 Hz), 2.88 (s, 3H).

후처리

  1. temperaturewas refluxed 8 h
  2. extractionThe mixture was extracted with ethyl acetate (50 ml)
  3. washthe organics were washed with brine (10 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-0cd916620251478f9a2203e93a0bf031
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531491B1

반응 노트

불러오는 중…