Allyl bromide → HCID 58269933, compound

HRID 602531Notes

Reaction equation

HRID 602531 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[N:5]=[C:4]([Cl:10])[C:3]=1[NH2:11].[H-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1C(=O)CCC1>[CH2:16]([NH:11][C:3]1[C:4]([Cl:10])=[N:5][C:6]([Br:9])=[C:7]([CH3:8])[C:2]=1[Br:1])[CH:15]=[CH2:14]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 58269942HCID 58269942, compound

Product 1

HCID 58269933HCID 58269933, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4,6-dibromo-2-chloro-5-methyl-pyridin-3-ylamine (9.3 g, 31 mmol) and tetrabutylammonium bromide (1.0 g, 3.1 mmol) in anhydrous NMP (30 mL) is added NaH (60%, 1.5 g, 37.5 mmol) in one portion at 0° C. The mixture is gradually warmed to room temperature and stirred for two hours, then treated with allyl bromide (3.3 mL, 37.5 mmol) at 0° C., and stirred at 60° C. for three hours. The reaction mixture is cooled and partitioned between EtOAc and water. The organic layer is separated washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Chromatography of the residue on silica gel (Hexane/EtOAc, 10:1) gives allyl-(4,6-dibromo-2-chloro-5-methyl-pyridin-3-yl)-amine.

Workup

  1. stirringstirred at 60° C. for three hours
  2. temperatureThe reaction mixture is cooled
  3. custompartitioned between EtOAc and water
  4. customThe organic layer is separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c36d3b2f5bb499793215bdf0864d828
Source dataset
uspto-grants-2011_03
Patent number
US07906528B2

Reaction notes

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