Sodium Carbonate → 4-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde

HRID 1851165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851165
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][N:5]2[N:15]=[C:16]([CH3:18])[N:17]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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]>[F:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([C:24]3[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=3)=[N:3][C:4]3[N:5]([N:15]=[C:16]([CH3:18])[N:17]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 867030255-Chloro-6-(3-fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Produkt 1

HCID 867030534-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehydeAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of 0.73 g (2.8 mmol) 5-chloro-6-(3-fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 458.3 mg (3.1 mmol) 4-formylphenylboronic acid in 14 mL 1,2-dimethoxyethane are added 5.2 mL of a sodium carbonate solution (10%) and 102 mg (0.13 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture is heated to 90° C. under an inert gas atmosphere over night. The reaction mixture is diluted with water and extracted three times with dichloromethane. The combined organic layers are washed with brine and dried over sodium sulphate. After evaporation of the solvent the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield 0.85 g (87.3%) of the desired aldehyde.

Aufarbeitung

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulphate
  4. customAfter evaporation of the solvent the residue
  5. customis purified by chromatography on silica gel (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-407df0aba34843ff99af2e2d4a3a7710
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957064B2

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