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

HRID 1970953노트

반응식

HRID 1970953 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-207e86fea42e4098b41c703e453cac89
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431578B2

반응 노트

불러오는 중…