N-Iodosuccinimide → Ethyl 6-iodo-3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 880029노트

반응식

HRID 880029 반응식
[CH3:1][O:2][C:3]1[C:4](=[O:15])[N:5]([CH3:14])[CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C1C(=O)N([I:23])C(=O)C1>CN(C=O)C.C(Cl)Cl>[I:23][C:6]1[N:5]([CH3:14])[C:4](=[O:15])[C:3]([O:2][CH3:1])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1

참가 물질

5

반응물 2

HCID 120273N-Iodosuccinimide2회HCID 15122761Ethyl 3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

생성물 1

HCID 86730083Ethyl 6-iodo-3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate수율 50.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of Intermediate 1 (101 mg, 0.478 mmol) in DMF (0.5 mL) was added NIS (108 mg, 0.478 mmol) at rt. The reaction was stirred at rt for 3 days. An additional equivalent of NIS (67 mg, 0.30 mmol) was added and the reaction mixture heated at 60° C. overnight. The reaction was allowed to cool, diluted with DCM (40 mL) and the organic portion washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in a small amount of DCM and charged to a 12 g silica gel cartridge which was eluted with a 25 min gradient from 0-100% EtOAc/hexane to give Intermediate 19A (81 mg, 50% yield) as a yellow solid.

후처리

  1. temperaturethe reaction mixture heated at 60° C. overnight
  2. temperatureto cool
  3. washthe organic portion washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in a small amount of DCM
  8. additioncharged to a 12 g silica gel cartridge which
  9. washwas eluted with a 25 min gradient from 0-100% EtOAc/hexane

출처 및 근거

ORD 기록
ord-d22294cb9e67446b814a614de33554f1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993557B2

반응 노트

불러오는 중…