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Potassium Carbonate → HCID 59632933, Verbindung

HRID 2369093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2369093
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[N:6][CH:7]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[K+].[K+]>COCCOC.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:33]=3)=[CH:7][N:6]=2)=[CH:9][C:10]([C:20]([O:22][CH3:23])=[O:21])=[N:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59632248HCID 59632248, Verbindung

Produkt 1

HCID 59632933HCID 59632933, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Methyl 5-(5-bromopyridin-2-yl)-1-(2-chlorophenyl)-1H-pyrazole-3-carboxylate (200 mg, 0.51 mmol), 3-(methylsulfonyl)phenylboronic acid (120 mg, 0.60 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (11) dichloromethane adduct (20 mg, 24 μmol), and K2CO3 (0.45 mL of a 3.5M aqueous solution, 1.6 mmol) were combined in DME (2.5 mL) in a microwave reaction vessel. The dark mixture was heated at 120° C. for 5 minutes. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was removed and extracted with additional EtOAc. The combined organics were dried over Na2SO4, treated with some decolorizing carbon and filtered through a pad of Celite. Concentration of the filtrates under reduced pressure and purification by flash column chromatography eluting with 0% to 50% MeCN/CH2Cl2 afforded methyl 1-(2-chlorophenyl)-5-(5-(3-(methylsulfonyl)phenyl)pyridin-2-yl)-1H-pyrazole-3-carboxylate as a pale yellow foam. This material was carried on to the subsequent step. MS(ES): 468 [M+H]+.

Aufarbeitung

  1. customThe aqueous layer was removed
  2. extractionextracted with additional EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. additiontreated with some decolorizing carbon
  5. filtrationfiltered through a pad of Celite
  6. customConcentration of the filtrates under reduced pressure and purification by flash column chromatography
  7. washeluting with 0% to 50% MeCN/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-76a2f60fb5214ddaad7c364b20e295fe
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08703805B2

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