Pivaloyl chloride → 1-(5-Bromo-pyridin-3-yl)-4,4-dimethyl-pent-1-yn-3-one

HRID 1970953Notes

Reaction equation

HRID 1970953 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:7]=1.[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C.[Cu]Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 665244243-Bromo-5-((trimethylsilyl)ethynyl)pyridine

Product 1

HCID 687701071-(5-Bromo-pyridin-3-yl)-4,4-dimethyl-pent-1-yn-3-one

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Bromo-5-trimethylsilanylethynyl-pyridine (1.0 eq, 1.22 g, 4.78 mmol), pivaloyl chloride (1.1. eq, 0.647 ml, 5.26 mmol) and copper(I) chloride (0.2 eq, 95 mg, 0.96 mmol) are dissolved in DMF (8 ml). The resulting mixture is heated using microwave radiation at 120° C. for 30 min. The mixture is filtered and washed with EtOAc. The filtrate is concentrated in vacuo and partitioned between sat. aqueous NaHCO3 solution and EtOAc. The organic portion is separated, dried (MgSO4) and concentrated in vacuo to afford the title compound; [M+H]+=266/268.

Workup

  1. temperatureThe resulting mixture is heated
  2. customat 120° C.
  3. customfor 30 min
  4. filtrationThe mixture is filtered
  5. washwashed with EtOAc
  6. concentrationThe filtrate is concentrated in vacuo
  7. custompartitioned between sat. aqueous NaHCO3 solution and EtOAc
  8. customThe organic portion is separated
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-207e86fea42e4098b41c703e453cac89
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

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