1-Ethenyl-3-methylbenzene → HCID 69945928, Verbindung

HRID 724930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724930
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[CH2:26].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH:26]=[CH:25][C:24]3[CH:23]=[C:22]([CH3:21])[CH:29]=[CH:28][CH:27]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

Komponenten

8

Edukt 3

HCID 75291-Ethenyl-3-methylbenzeneHCID 516892Sodium BicarbonateHCID 10547779HCID 10547779, Verbindung

Produkt 1

HCID 69945928HCID 69945928, VerbindungAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.15 g, 0.4 mmol), 3-methylstyrene (0.05 mL, 0.4 mmol), palladium acetate (29 mg, 0.13 mmol), sodium bicarbonate (83 mg, 1.0 mmol), tetrabutylammonium chloride (0.11 g, 0.47 mmol), and 1 crystal of BHT in 2 mL of N,N-dimethylformamide was heated at 90° C. under argon for 4.5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and concentrated. Purification by flash chromatography, eluting with ethyl acetate/hexanes, afforded 0.13 g of the title compound, m.p. 207°-208° C. (ethyl acetate/hexanes).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customPurification by flash chromatography
  6. washeluting with ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0f3af44016464a439aa6424a5b78f39e
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705499

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