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

HRID 923480Notes

Reaction equation

HRID 923480 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-028586114a174a939c375347c41a4ded
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…