Potassium Carbonate → 6-Methyl-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

HRID 2113630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113630
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19].[CH3:20]B(O)O.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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.O>[CH3:20][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 139377Methylboronic AcidHCID 586281896-Chloro-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

Produkt 1

HCID 586281916-Methyl-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

In a sealed tube, dissolve 6-chloro-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carbonitrile (242 mg, 0.853 mmol), CH3B(OH)2 (300 mg, 5.10 mmol), K2CO3 (1.6 g, 12 mmol), and Pd(PPh3)4 in a solution of dioxane (10 mL) and H2O (2 mL). Bubble argon through the mixture for 30 minutes and seal. Heat the mixture at 115° C. overnight. Cool the mixture to room temperature. Add H2O (20 mL) and extract with EtOAc (3×20 mL). Combine the organic extracts and wash with brine (60 mL). Dry the organic layer over Na2SO4 and remove the solvent under reduced pressure. Purify the crude product using silica gel chromatography eluting with EtOAc/hexane (1:1) to yield the title compound. MS 264.07 (M+1).

Aufarbeitung

  1. customseal
  2. temperatureCool the mixture to room temperature
  3. extractionAdd H2O (20 mL) and extract with EtOAc (3×20 mL)
  4. washCombine the organic extracts and wash with brine (60 mL)
  5. dry with materialDry the organic layer over Na2SO4
  6. customremove the solvent under reduced pressure
  7. customPurify the crude product
  8. washeluting with EtOAc/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6fee241b24664faa8a6bba38cc01b94c
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432275B2

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