N-Iodosuccinimide → 7-Chloro-3-iodoimidazo[1,2-a]pyridine

HRID 341247

반응식

HRID 341247 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[I:11]N1C(=O)CCC1=O>CN(C=O)C.O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([I:11])=[CH:9][N:10]=[C:4]2[CH:3]=1

참가 물질

6

반응물 2

HCID 120273N-IodosuccinimideHCID 196959017-Chloroimidazo(1,2-a)pyridine

생성물 1

HCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridine수율 75.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 7-Chloro-imidazo[1,2-a]pyridine (30.9 g, 186 mmol, 1.0 equiv) in DMF (280 ml) was added N-iodosuccinimide (43.6 g, 194 mmol, 1.05 equiv) and the resulting mixture was stirred overnight at RT. The thin brown slurry was diluted with water (840 ml), brine (280 ml) and extracted with EtOAc (560 ml). The aqueous was further extracted with EtOAc (3×280 ml). The combined organic phases were washed with water (2×280 ml), 10% w/v sodium thiosulfate (280 ml), brine (280 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown residue. The residue was triturated with ether (200 ml), filtered and the solid was washed ether (2×50 ml) and dried on the filter to give 39 g of product. MS: [M+H]+ 279

후처리

  1. extractionextracted with EtOAc (560 ml)
  2. extractionThe aqueous was further extracted with EtOAc (3×280 ml)
  3. washThe combined organic phases were washed with water (2×280 ml), 10%
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown residue
  8. customThe residue was triturated with ether (200 ml)
  9. filtrationfiltered
  10. washthe solid was washed ether (2×50 ml)
  11. customdried on the
  12. filtrationfilter

출처 및 근거

ORD 기록
ord-ec0333197fe042abba71d365ce1829c1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895745B2

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