Reaktion #89147

Reaktionsgleichung

rac-cis-(2-bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone

2-(tributylstannyl)pyrimidine

Cs2CO3

→

title compound

rac-cis-(3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone

TFA

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed for 5 min
2. 2
   SonstigeThe completion of reaction
3. 3
   TemperaturThe mixture was cooled
4. 4
   Extraktionextracted with EtOAc
5. 5
   WaschenThe combine organic layers were washed with saturated NaHCO3
6. 6
   Trocknendried over Na2SO4
7. 7
   SonstigeThe solvent was removed in vacuo
8. 8
   Sonstigeto obtain the crude, which
9. 9
   Sonstigewas purified by preparative-HPLC

Vorschrift

The mixture of rac-cis-(2-bromo-5-methylphenyl)(3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone (0.03 g, 0.0638 mmol), 2-(tributylstannyl)pyrimidine (0.028 g, 0.0766 mmol), P(PPh3)4 (0.011 g, 0.01 mmol), Cs2CO3 (0.42 g, 0.13 mmol) and dioxane (1 mL) was degassed for 5 min and heated overnight at 140° C. oil bath. The completion of reaction was monitored by analytical HPLC. The mixture was cooled and extracted with EtOAc. The combine organic layers were washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude, which was purified by preparative-HPLC to obtain the title compound as TFA salt. ESI-MS (m/z): 470, [M+1]+.

Quelle