Potassium Fluoride → 6-(1-Ethoxy-vinyl)-nicotinonitrile

HRID 1191087ノート

反応式

HRID 1191087 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH2:10]([O:12][C:13]([Sn](CCCC)(CCCC)CCCC)=[CH2:14])[CH3:11].[F-].[K+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:13]([O:12][C:10]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)=[CH2:11])[CH3:14]

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 50057186-Bromopyridine-3-carbonitrile

生成物 1

HCID 598289076-(1-Ethoxy-vinyl)-nicotinonitrile収率 190.5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

Slurry 6-bromo-nicotinonitrile (8.0 g, 43.7 mmol), 1-ethoxyvinyl-tributylstannane (17.4 g, 48 mmol), and dichlorobis(triphenylphosphine)-palladium (1.5 g, 2.2 mmol) in acetonitrile (680 mL) at room temperature. Stir the mixture at reflux for 16 h under a nitrogen atmosphere. Cool the mixture to room temperature, add aqueous saturated potassium fluoride (100 mL), stir 30 min then filter and wash with EtOAc (200 mL). Wash the organic phase with water (250 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (14.5 g) that was used without further purification. MS (ES+) m/z: 175 (M+H)+.

後処理

  1. customat room temperature
  2. temperatureat reflux for 16 h under a nitrogen atmosphere
  3. stirringstir 30 min
  4. filtrationthen filter
  5. washwash with EtOAc (200 mL)
  6. washWash the organic phase with water (250 mL)
  7. dry with materialDry the organic layer over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-915c87f2b3024d70ac469c4727470327
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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