Sodium Carbonate → 6-(4-(Methylsulfonyl)phenyl)pyridin-3-ol

HRID 423611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423611
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:15]1[N:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[N:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 27628652-Bromo-5-hydroxypyridine

Produkt 1

HCID 532295926-(4-(Methylsulfonyl)phenyl)pyridin-3-olAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(4-Methylsulfonylphenyl)boronic acid (4.40 g, 21.55 mmol) was added to a solution of 6-bromo-3-pyridinol (2.5 g, 14.37 mmol) in DME (125 mL), followed by addition of 2M Na2CO3 (75 mL) and Pd(PPh3)4 (0.83 g, 0.72 mmol). The reaction mixture was degassed with N2 and heated at 80° C. overnight, then cooled to ambient temperature. Water (50 mL), 1N NaOH (50 mL), brine (50 mL) and CH2Cl2 (150 mL) were added. The CH2Cl2 layer was separated and the aqueous layer was washed with CH2Cl2 (100 mL). The combined CH2Cl2 extract was further washed with a mixture of water (50 mL), 1N NaOH (50 mL) and brine (50 mL). The aqueous layers were combined and washed with CH2Cl2 (100 mL), neutralized with concentrated HCl and extracted with EtOAc (250 mL×2). The combined EtOAc extract was filtered through celite on top of a layer of silica gel, which was further washed with EtOAc (100 mL). The EtOAc filtrate was washed with brine and dried over Na2SO4, filtered, and concentrated to a light yellow solid, which was triturated with small amount of hot MeOH to give 2.20 g (61%) of 6-[4-(methylsulfonyl)phenyl]-3-pyridinol as a white solid.

Aufarbeitung

  1. customThe reaction mixture was degassed with N2
  2. temperaturecooled to ambient temperature
  3. additionWater (50 mL), 1N NaOH (50 mL), brine (50 mL) and CH2Cl2 (150 mL) were added
  4. customThe CH2Cl2 layer was separated
  5. washthe aqueous layer was washed with CH2Cl2 (100 mL)
  6. extractionThe combined CH2Cl2 extract
  7. washwas further washed with a mixture of water (50 mL), 1N NaOH (50 mL) and brine (50 mL)
  8. washwashed with CH2Cl2 (100 mL)
  9. extractionextracted with EtOAc (250 mL×2)
  10. extractionThe combined EtOAc extract
  11. filtrationwas filtered through celite on top of a layer of silica gel, which
  12. washwas further washed with EtOAc (100 mL)
  13. washThe EtOAc filtrate was washed with brine
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated to a light yellow solid, which
  17. customwas triturated with small amount of hot MeOH

Quellen und Nachweise

ORD-Eintrag
ord-60555765dcea48f68dfa55bb6ccd6a47
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

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