Reaktion #157161

Reaktionsgleichung

methyl 3-amino-6-bromopicolinate

cyclohexyl zincbromide

THF

→

methyl 3-amino-6-cyclohexylpicolinate

Ausbeute 98.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction was filtered
2. 2
   Waschenwashed with EtOAc
3. 3
   WaschenThe organic was washed with H2O (100 mL), NaCl(sat.) (50 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   Sonstigethe volatiles were removed in vacuo
6. 6
   SonstigeThe product was purified on silica utilizing the Isco 0-65% gradient of hexane/EtOAc

Vorschrift

A solution of methyl 3-amino-6-bromopicolinate (1.0 equiv.), cyclohexyl zincbromide 0.5 M solution in THF (1.5 equiv.), and tetrakis(triphenylphosphine)-palladium(0) (0.05 equiv.) was stirred at 50° C. for 15 minutes. The reaction was filtered and washed with EtOAc. The organic was washed with H2O (100 mL), NaCl(sat.) (50 mL), dried over MgSO4, and the volatiles were removed in vacuo. The product was purified on silica utilizing the Isco 0-65% gradient of hexane/EtOAc to yield methyl 3-amino-6-cyclohexylpicolinate (98%). LCMS (m/z): 235.2 (MH+); LC Rt=1.89 min.

Quelle