Potassium Carbonate → Tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4'-bipiperidine-1'-carboxylate

HRID 407896노트

반응식

HRID 407896 반응식
Br[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:3]1=[O:21].C([O-])([O-])=O.[K+].[K+].[Br:28][C:29]1[C:34]([F:35])=[CH:33][C:32]([OH:36])=[C:31]([F:37])[CH:30]=1>CN(C=O)C.O.CCOC(C)=O>[Br:28][C:29]1[C:34]([F:35])=[CH:33][C:32]([O:36][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[C:3]2=[O:21])=[C:31]([F:37])[CH:30]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 70180424-Bromo-2,5-difluorophenolHCID 86688083Tert-butyl 3-bromo-2-oxo-1,4'-bipiperidine-1'carboxylate

생성물 1

HCID 66803528Tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4'-bipiperidine-1'-carboxylate수율 73%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of tert-butyl 3-bromo-2-oxo-1,4′-bipiperidine-1′carboxylate (723 mg, 2.00 mmol) in DMF (5 mL) was added K2CO3 (553 mg, 4.00 mmol) and 4-bromo-2,5-difluorophenol (460 mg, 2.20 mmol). The reaction was heated at 60° C. overnight. The reaction was cooled and diluted with water and EtOAc. The organic layer was separated and the aqueous washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated. The crude residue was purified over silica gel (2:1 hexanes/EtOAc) to give tert-butyl 3-(4-bromo-2,5-difluorophenoxy)-2-oxo-1,4′-bipiperidine-1′-carboxylate (710 mg, 73%) as a white solid.

후처리

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. washthe aqueous washed with EtOAc
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude residue was purified over silica gel (2:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-200bb0d81cbf451086bc699006b70819
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754226B2

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