Sodium Carbonate → 2-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazine

HRID 1269632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269632
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>C(COC)OC.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>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)[N:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Produkt 1

HCID 184483272-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazineAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2,6-dichloropyrazine (0.5 g, 3.36 mmol), sodium carbonate (0.925 g, 8.73 mmol) and 4-trifluoromethylphenylboronic acid (0.638 g, 3.36 mmol) in dimethoxyethane (15 mL) and water (7.5 mL) under nitrogen was added tetrakis(triphenylphosphine) palladium (0) (0.078 g). The resulting mixture was heated at reflux for 5 h under nitrogen, before stirring at room temperature overnight. The reaction was diluted with water (50 mL) and extracted with chloroform (2×75 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) 10:1–6:1 cyclohexane:EtOAc afforded the title compound as a white solid (0.317 g).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 h under nitrogen
  3. extractionextracted with chloroform (2×75 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customPurification by Biotage™ chromatography (Silica, 90 g) 10:1–6:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-95d5904f7e594812983978ced455bd3a
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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