Sodium Carbonate → 5-(4-Chlorophenyl)-2-methylpyridine

HRID 1590094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590094
[C:1]1([C:7]2[CH:12]=[N+:11]([O-])[C:10]([CH3:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-].[Cl:23]C1C=CC(B(O)O)=CC=1>C1(C)C=CC=CC=1.[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.CCO>[Cl:23][C:4]1[CH:5]=[CH:6][C:1]([C:7]2[CH:8]=[CH:9][C:10]([CH3:14])=[N:11][CH:12]=2)=[CH:2][CH:3]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 433294Lithium ChlorideHCID 149805285-Phenyl-2-picoline N-oxide

Produkt 1

HCID 123670755-(4-Chlorophenyl)-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The trifluoromethane sulfonate from Step 1 (500 mg) was dissolved in 10 mL of toluene, 5 mL of EtOH, and 1.6 mL of 2M aqueous Na2CO3. Then 203 mg LiCl, 411 mg of 4-chlorobenzeneboronic acid (Lancaster) and 832 mg of tetrakis (triphenylphosphine) palladium were added successively. The resulting reaction mixture was heated up to 90°-95° C. for 1 hour. The reaction mixture was cooled down to room temperature, EtOAc was added and the organic phase was washed with 1N NaOH, brine, dried over MgSO4, filtered and concentrated. Purification by flash chromatography using hexane:EtOAc 3:2 gave the title compound.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated up to 90°-95° C. for 1 hour
  3. washthe organic phase was washed with 1N NaOH, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9a1ce540832d42acad73b1a8bff37a48
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202321

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