Hexane → 5-Bromo-2-(3,4-dimethoxyphenyl)pyridine

HRID 1907695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907695
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].C(=O)([O-])[O-].[Na+].[Na+].CCCCCC>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[C:16]([O:17][CH3:18])[CH:15]=2)=[N:3][CH:4]=1

Komponenten

9

Edukt 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 27347023,4-Dimethoxyphenylboronic acid

Produkt 1

HCID 139797415-Bromo-2-(3,4-dimethoxyphenyl)pyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a degassed solution of 2,5-dibromopyridine 35 (0.50 g, 2.11 mmol), 3,4-dimethoxyphenylboronic acid 36 (0.50 g, 2.74 mmol) and sodium carbonate (0.67 g, 6.3 mmol) in ethyleneglycol dimethylether (7 mL) and H2O (2 mL) was added tetrakis(triphenylphosphine)-palladium(0) (0.16 g, 0.14 mmol) and the solution was stirred at 75° C. for 18 h. The reaction mixture was filtered, concentrated, diluted with AcOEt, washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography of the residue (eluent: 3:1 hexane:AcOEt) provided title compound 37 (0.47 g, 76% yield).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b8b1e079f9094a7d8e7d213873616319
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598168B2

Notizen zur Reaktion

Wird geladen…