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N-Iodosuccinimide → 2-Chloro-6-fluoro-3-iodoimidazo[1,2-A]pyridine

HRID 705072
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HRID 705072 반응식
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[CH:11]=1.[I:12]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1[I:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 552678642-Chloro-6-fluoroimidazo[1,2-A]pyridine

생성물 1

HCID 717433442-Chloro-6-fluoro-3-iodoimidazo[1,2-A]pyridine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of the title compound from Example 2 Step B (1.0 g, 5.86 mmol) in acetonitrile (29.3 mL) was added N-iodosuccinimide (1.583 g, 7.04 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 (10-30% ethyl acetate in hexanes) provided the title compound: LCMS m/z 296.70 [M+H]+, 298.65 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.03 (t, J=2.8 Hz, 1H), 7.56-7.51 (m, 1H), 7.22-7.18 (m, 1H).

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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 (10-30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0875119397c24a428376bd3bfae1ea14
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09173873B2

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