Sodium Carbonate → 4-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 503723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503723
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[CH:14]=[CH:15][N:16]=[C:4]2[N:3]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.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]>[C:8]1([C:7]2[C:2]([C:22]3[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=3)=[N:3][C:4]3[N:5]([CH:14]=[CH:15][N:16]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 772315047-Chloro-6-phenylimidazo[1,2-a]pyrimidine

Produkt 1

HCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 6 g of the crude product obtained in step 3 and 5.1 g 4-formylphenylboronic acid in 210 ml 1,2-dimethoxyethane are added 0.96 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct and 42 ml of a 10% w/w sodium carbonate solution. The resulting mixture is heated to 80° C. under an inert gas atmosphere for 15 h. The work up is performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers are dried over sodium sulphate and evaporated. The residue is suspended in ethyl acetate and the resulting mixture stirred for 2 h at room temperature. The product is collected by filtration and used without further purification.

Aufarbeitung

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers are dried over sodium sulphate
  4. customevaporated
  5. filtrationThe product is collected by filtration
  6. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d9c8d2c30ca3428db93799f5ea39b238
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776864B2

Notizen zur Reaktion

Wird geladen…