5-Methyl-2-(tri-n-butylstannyl)pyridine → Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

HRID 1845285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845285
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6](Br)[CH:5]=1.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([Sn](CCCC)(CCCC)CCCC)=[N:18][CH:19]=1>C1(C)C=CC=CC=1.CN(C=O)C.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>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([C:17]2[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][N:18]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:12]

Komponenten

7

Edukt 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Produkt 1

HCID 58188160Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-5-hydroxy-benzoic acid methyl ester (1.47 g, 6.36 mmol), 5-methyl-2-(tributylstannyl)pyridine (3.0 g, 7.85 mmol), tetrakis(triphenylphosphine)-palladium(0) (300 mg, 0.26 mmol) in toluene (20 mL) and DMF (2 mL) was subjected to microwave irradiation at 110° C. for 1 hour. After cooling, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound as a white solid.

Aufarbeitung

  1. customirradiation at 110° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-87a7dd84bd19447c9e3e78f5415f280d
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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