Sodium Bicarbonate → 6-[5-(Methylsulfonyl)-3-pyridinyl]-4-(4-pyridinyl)quinoline

Participants

Reaction Steps

A mixture of (6-bromo-4-(4-pyridinyl)quinoline (250 mg, 0.88 mmol), 5-methylsulfonyl pyridine-3-boronic acid (201 mg, 1.0 mmol), tetrakistriphenylphosphine palladium (0) (104 mg, 0.09 mmol), and sat. aqueous NaHCO3 (1.75 mL), in dioxane (5 mL) was heated at 110° C. for 1 h then cooled to room temperature. The r×n was filtered through Celite and Na2SO4 onto silica and the crude product was purified by column chromatography (5% EtOAc/Hex-10% Ethanol/EtOAc; 30 min gradient). Evaporation and precipitation from MeOH/water (2/98) provided the title compound as a yellow solid. (160 mg, 50%). ESMS [M+H]+=362.1

Provenance & Evidence