Reaktion #69558

Reaktionsgleichung

3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxy-N-propylpyrazolo[5,1-b][1,3]thiazole-7-amine

4-chloropyridine hydrochloride

sodium tert-butoxide

potassium phosphate tribasic

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

→

title compound

Ausbeute 58.7%

3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxy-N-propyl-N-pyridin-4-ylpyrazolo[5,1-b][1,3]thiazole-7-amine

Ausbeute 58.7%

Lösungsmittel

water

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas returned to room temperature
2. 2
   Extraktionthe reaction mixture was extracted with ethyl acetate
3. 3
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
4. 4
   SonstigeThe residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate

Vorschrift

To a 1,4-dioxane (0.7 mL) solution of 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxy-N-propylpyrazolo[5,1-b][1,3]thiazole-7-amine (70 mg, 0.179 mmol) were added 4-chloropyridine hydrochloride (32.2 mg, 0.215 mmol), sodium tert-butoxide (20.6 mg, 0.215 mmol), potassium phosphate tribasic (64.6 mg, 0.304 mmol), tris(dibenzylideneacetone)dipalladium (8.2 mg, 0.009 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (7.77 mg, 0.0134 mmol), and the mixture was stirred at 100° C. for seven hours. After the reaction mixture was returned to room temperature, water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate, and the solvent was distilled off under reduced pressure. The residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate: 10% then 80%) to obtain the title compound (49.4 mg, 0.105 mmol).

Quelle