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

HRID 1970953ノート

反応式

HRID 1970953 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-207e86fea42e4098b41c703e453cac89
出典データセット
uspto-grants-2013_04
特許番号
US08431578B2

反応ノート

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