Pivaloyl chloride → N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

HRID 1042334Notes

Reaction equation

HRID 1042334 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:11](=[O:12])[C:10]([CH3:15])([CH3:14])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 9921361N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromopyridin-2-amine (10 g, 57.79 mmol, 1 eq.) in 150 ml of DCM were added TEA (17.54 g, 173.3 mmol, 3 eq.) and 2,2-dimethylpropionyl chloride (10.45 g, 86.69 mmol, 1.5 eq.) dropwise. The temperature rose slowly. The reaction was stirred overnight at r.t. The white solid was removed by filtration and the solvent was evaporated. The crude was dissolved in with EtOAc and washed with 0.1N aq. HCl, sat. aqueous NaHCO3. The organics were dried over MgSO4 and concentrated. The resulting solid was recrystallized in EtOAc to give N-(6-bromopyridin-2-yl)-2,2-dimethylpropanamide (13.52 g, 91% yield) as a white solid.

Workup

  1. customThe white solid was removed by filtration
  2. customthe solvent was evaporated
  3. dissolutionThe crude was dissolved in with EtOAc
  4. washwashed with 0.1N aq. HCl, sat. aqueous NaHCO3
  5. dry with materialThe organics were dried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting solid was recrystallized in EtOAc

Sources & evidence

ORD record
ord-0104efab39ef4a76aa8e8c3f2f4bac71
Source dataset
uspto-grants-2013_10
Patent number
US08557849B2

Reaction notes

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