Potassium Phosphate, Tribasic → (3-(5-Methylpyridin-2-yl)phenyl)methanol

HRID 2088403

Reaktionsgleichung

Reaktionsgleichung von HRID 2088403
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1.[OH:17][CH2:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([C:23]2[CH:24]=[C:19]([CH2:18][OH:17])[CH:20]=[CH:21][CH:22]=2)=[N:11][CH:12]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 5642162-Bromo-5-methylpyridineHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Produkt 1

HCID 56604357(3-(5-Methylpyridin-2-yl)phenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

92 mg (0.08 mmol) of tetrakis(triphenylphosphine)palladium are added to a suspension, kept under nitrogen, of 849 mg (4.0 mmol) of tripotassium phosphate, 344 mg (2.0 mmol) of 2-bromo-5-methylpyridine and 304 mg (2.0 mmol) of 3-hydroxymethylbenzeneboronic acid in 12 ml of dioxane and 1 ml of water, and the mixture is heated at the boil with stirring for 18 hours. The reaction mixture is cooled to room temperature and partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate, evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: [3-(5-methylpyridin-2-yl)phenyl]methanol as yellowish oil; LCMS 200.

Aufarbeitung

  1. temperaturethe mixture is heated at the boil
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-358414a1b6004d7abe093fc8b5d47d65
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435986B2

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