StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Carbonate → N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide

HRID 2359110
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2359110
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH:10]=2)O1.[CH2:21]([N:23]1[CH:27]=[C:26](I)[C:25]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[N:24]1)[CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH2:21]([N:23]1[CH:27]=[C:26]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH:10]=2)[C:25]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[N:24]1)[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 497605002-Propionamidopyridine-4-Boronic Acid Pinacol EsterHCID 672606401-ethyl-4-iodo-3-(2-thienyl)-1H-pyrazole

Produkt 1

HCID 67260817N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamideAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanamide (0.60 mmol) and bis(tricyclohexylphosphine)palladium(II) chloride (0.05 mmol) were weighed into a microwave vial (reaction volume 2-5 mL). A solution of 1-ethyl-4-iodo-3-(2-thienyl)-1H-pyrazole (0.50 mmol) in 3.3 mL degassed dioxane and 1.1 mL of a degassed 2 M aqueous sodium carbonate solution were added. The reaction mixture was purged with argon, the microwave vial was capped with a septum and transferred to a laboratory microwave oven. The reaction mixture was irradiated to a reaction temperature of 120° C. for 15 min. After cooling to room temperature, the reaction mixture was diluted with water and extracted with dichloromethane. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5 to 0:100) to afford 152 mg N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide (93% yield).

Aufarbeitung

  1. additionwere added
  2. customThe reaction mixture was purged with argon
  3. customthe microwave vial was capped with a septum
  4. customtransferred to a laboratory microwave oven
  5. customThe reaction mixture was irradiated to a reaction temperature of 120° C. for 15 min
  6. additionthe reaction mixture was diluted with water
  7. extractionextracted with dichloromethane
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5 to 0:100)

Quellen und Nachweise

ORD-Eintrag
ord-f1671475fdf04f96bfaecd27f7d54da3
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685974B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion