Nitrogen → 4-(6-Bromo-2-pyridinyl)-1-methyl-4-piperidinol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol) in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15.

Provenance & Evidence