Reaktion #90758

Reaktionsgleichung

1-bromo-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-7-yl)imidazo[1,5-a]pyrazin-8-amine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

K2CO3

→

4-(8-amino-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

Ausbeute 54.8%

Lösungsmittel

dioxane H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeRemove the solvent in vacuo
2. 2
   workup.ADDITIONThe mixture was treated with ethyl acetate and water
3. 3
   Sonstigethe organic layer was separated
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenthe filtrate was concentrated
7. 7
   SonstigeThe residue was purified by preparative HPLC separation

Vorschrift

The mixture of 1-bromo-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-7-yl)imidazo[1,5-a]pyrazin-8-amine (200 mg, 0.497 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (194.54 mg, 0.497 mmol), Pd(dppf)Cl2 (18.3 mg, 0.025 mmol) and K2CO3 (137.26 mg, 0.995 mmol) in dioxane/H2O (5 mL/0.5 mL) was stirred at 90° C. for 2 h under nitrogen atmosphere. Remove the solvent in vacuo. The mixture was treated with ethyl acetate and water, the organic layer was separated, dried over sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by preparative HPLC separation to give 4-(8-amino-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (0.16 g, yield 50%).

Quelle