N-Iodosuccinimide → 2-Chloro-3-iodopyrazolo[1,5-A]pyridine

HRID 530015노트

반응식

HRID 530015 반응식
[Cl:1][C:2]1[CH:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[I:11]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[C:10]([I:11])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 122844332-Chloropyrazolo[1,5-a]pyridine

생성물 1

HCID 717433402-Chloro-3-iodopyrazolo[1,5-A]pyridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-chloro-pyrazolo[1,5-a]pyridine (0.500 g, 3.28 mmol) in acetonitrile (16.4 mL) was added N-iodosuccinimide (0.885 g, 3.93 mmol). The resulting mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound. LCMS m/z 278.72 [M+H]+, 280.64 [M+2+H]+, 1H NMR (500 MHz, CDCl3) 8.35 (d, J=6.8 Hz, 1 H), 7.38 (d, J=9.0 Hz, 1H), 7.24 (d, J=8.6 Hz, 1 H), 6.84-6.81 (m, 1 H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-7895939d8b494ae0b01a25432ada00a1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351973B2

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