Potassium Carbonate → HCID 58516004, Verbindung

HRID 717847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717847
Cl[C:2]1[N:11]=[C:10]([C:12]#[N:13])[C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([F:22])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:14][C:9]1[C:10]([C:12]#[N:13])=[N:11][C:2]([C:18]2[CH:17]=[C:16]([F:15])[CH:21]=[C:20]([F:22])[CH:19]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 58515970HCID 58515970, Verbindung

Produkt 1

HCID 58516004HCID 58516004, VerbindungAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of methyl 2,5-dichloro-6-cyanonicotinate (2.0 g, 8.6 mmol), (3,5-difluorophenyl)boronic acid (1.5 g, 9.5 mmol) and potassium carbonate (2.6 g, 19 mmol) in water (16 mL) and 1,4-dioxane (41 mL) were bubbled with nitrogen gas (10 minutes). Bis(triphenylphosphine)palladium(II) chloride (0.67 g, 0.95 mmol) was added and the mixture was bubbled with nitrogen gas (10 minutes). The mixture was heated at 80° C. for 1 hour and diluted with ethyl acetate and water. The aqueous layer was separated and extracted again with ethyl acetate. The combined extracts were washed with water, washed with brine, dried over sodium sulfate, filtered and evaporated. Purification on silica gel using ethyl acetate in hexanes (0-50%) gave the desired compound (2.5 g, 94%). LCMS calculated for C14H8ClF2N2O2 (M+H)+: m/z=309.0. found: 308.9.

Aufarbeitung

  1. customthe mixture was bubbled with nitrogen gas (10 minutes)
  2. additiondiluted with ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionextracted again with ethyl acetate
  5. washThe combined extracts were washed with water
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customPurification on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d5a22cbf794444edab29fcce5d1ddec3
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193721B2

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