Potassium Carbonate → 3-Methoxy-6-methyl-2-(3-trifluoromethylphenyl)-pyridine

HRID 1632014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1632014
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N:3]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C.O.COCCOC>[CH3:9][O:8][C:7]1[C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:12]([F:23])([F:22])[F:11])[CH:18]=2)=[N:3][C:4]([CH3:10])=[CH:5][CH:6]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 109655632-Bromo-3-methoxy-6-methylpyridine

Produkt 1

HCID 580200463-Methoxy-6-methyl-2-(3-trifluoromethylphenyl)-pyridineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To the 2-bromo-3-methoxy-6-methyl-pyridine synthesized above (1.2 g, 5.94 mmol), 3-trifluoromethylphenylboronic acid (1.69 g, 8.91 mmol), PPh3 (0.31 g, 1.19 mmol), K2CO3 (2.46 g, 17.82 mmol) and Pd(OAc)2 (0.13 g, 0.59 mmol) was added DME (15 mL), and EtOH—H2O (1:1, 6 mL). Ar gas was bubbled through the stirred reaction for 5 min. The reaction was stirred at 80° C. under Ar for 20 h. The reaction was cooled to room temperature, concentrated, and H2O and dichloromethane (40 mL each) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic extracts were dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 1:1 dichloromethane-hexanes then dichloromethane to afford 1.36 g (86%) of 3-methoxy-6-methyl-2-(3-trifluoromethyl-phenyl)-pyridine (I-4, Y═R1═CH3, R2═CF3) as a light yellow solid.

Aufarbeitung

  1. customAr gas was bubbled through the stirred reaction for 5 min
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. additionH2O and dichloromethane (40 mL each) were added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
  7. dry with materialThe combined organic extracts were dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-52804c00f90b4d0193cd399f84a2a72e
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791267B2

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