Water → Di-tert-butyl [(3-bromopyridin-4-yl)methyl]imidodicarbonate

HRID 923480노트

반응식

HRID 923480 반응식
[C:1]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[K+].[Br:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[CH2:29]Cl.O>CN(C=O)C>[Br:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[CH2:29][N:8]([C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

참가 물질

6

반응물 4

HCID 962WaterHCID 279800Di-tert-butyl IminodicarboxylateHCID 23665647Potassium tert-butoxideHCID 669333093-Bromo-4-(chloromethyl)pyridine

생성물 1

HCID 118318074Di-tert-butyl [(3-bromopyridin-4-yl)methyl]imidodicarbonate수율 90.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 1.73 g of di-tert-butyl imidodicarbonate in DMF 16 ml was added 894 mg of potassium tert-butoxide under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture was added a solution of 1.37 g of 3-bromo-4-(chloromethyl)pyridine in 3 ml of DMF under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.32 g of di-tert-butyl [(3-bromopyridin-4-yl)methyl]imidodicarbonate.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 2 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-028586114a174a939c375347c41a4ded
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278968B2

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