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

HRID 341247ノート

反応式

HRID 341247 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-ec0333197fe042abba71d365ce1829c1
出典データセット
uspto-grants-2014_11
特許番号
US08895745B2

反応ノート

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