Water → 7-(4-Fluoro-phenyl)-3-iodo-imidazo[1,2-a]pyridine

HRID 341230

반응식

HRID 341230 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.[I:17]N1C(=O)CCC1=O.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14]([I:17])=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 593207997-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridine

생성물 1

HCID 593207767-(4-Fluoro-phenyl)-3-iodo-imidazo[1,2-a]pyridine수율 29%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 7-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine (13.0 g, 61.3 mmol) in N,N-dimethylformamide (100 mL) stirring under a nitrogen atmosphere at ambient was added N-iodosuccinimide (14.5 g, 64.4 mmol). The reaction mixture was stirred for 2 h and then poured into water (1 L) and stirred for a further 30 min. The solid obtained was collected by filtration, washed with water and air dried on the filter. The solid was triturated with ether, collected by filtration and dried under vacuum at 50° C. The solid obtained was partitioned between water and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The solid thus obtained was partitioned between aqueous sodium thiosulphate solution and EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The product was triturated with EtOAc, collected by filtration and air-dried to afford 6.0 g (29%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.23 (1H, d), 7.91 (1H, s), 7.78 (1H, s), 7.67 (2H, dd), 7.28 (1H, d), 7.22 (2H, t). A further crop of product (11.0 g) containing minor impurities was obtained by evaporating the filtrates under reduced pressure, triturating with petrol/EtOAc and collection by filtration.

후처리

  1. stirringstirred for a further 30 min
  2. customThe solid obtained
  3. filtrationwas collected by filtration
  4. washwashed with water and air
  5. customdried on the filter
  6. customThe solid was triturated with ether
  7. filtrationcollected by filtration
  8. customdried under vacuum at 50° C
  9. customThe solid obtained
  10. customwas partitioned between water and EtOAc
  11. washThe organic layer was washed with brine
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe solid thus obtained
  16. customwas partitioned between aqueous sodium thiosulphate solution and EtOAc
  17. washThe organic layer was washed with brine
  18. dry with materialdried (MgSO4)
  19. concentrationconcentrated under reduced pressure
  20. customThe product was triturated with EtOAc
  21. filtrationcollected by filtration
  22. customair-dried

출처 및 근거

ORD 기록
ord-28ddd69c586946899a8a3707ac18036e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895745B2

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