Potassium Carbonate → 5-Bromo-2-(2-fluorophenyl)pyrimidine

HRID 42024

Reaktionsgleichung

Reaktionsgleichung von HRID 42024
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 70066515-Bromo-2-iodopyrimidine

Produkt 1

HCID 497586955-Bromo-2-(2-fluorophenyl)pyrimidineAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 5-bromo-2-iodopyrimidine (2.58 mmol, 0.500 g), 2-fluorophenylboronic acid (3.87 mmol, 0.542 g), 2M aqueous solution of K2CO3 (7.76 mmol, 3.9 ml), Pd(PPh3)4 in dioxane (12 ml) was heated at 110° C. overnight. The solvent was evaporated and the solid residue was extracted between water and ethyl acetate. The organic phase was evaporated and the crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.466 g (yield 56%) of the expected product.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe solid residue was extracted between water and ethyl acetate
  3. customThe organic phase was evaporated
  4. customthe crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-db65dc6d4e8a4422803c0cb854df8532
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

Verknüpfte Notizen

Wird geladen…