Sodium Carbonate → HCID 86692537, compound

Participants

Reaction Conditions

Reaction Steps

To 2,5-dibromo-3-methylpyridine (5.0 g), tetrakis(triphenylphosphine)palladium(0) (1.15 g), and N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (6.16 g) were added 1,4-dioxane (40 ml) and 2M aqueous solution of sodium carbonate (25 ml), stirred at 90° C. for 6 hours, then tetrakis(triphenylphosphine)palladium(0) (115 mg) was added thereto, and stirred at 90° C. for 1 hour. To the reaction solution was added water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester (4.83 g) as a pale yellow oil.

Provenance & Evidence