Cesium carbonate → 5,6'-Dimethyl-2,2'-bipyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (331 mg, 1.017 mmol), palladium acetate (5.71 mg, 0.025 mmol), 1,1′-bis(diphenylphosphino)ferrocene (28.5 mg, 0.051 mmol), copper(I)chloride (50.4 mg, 0.509 mmol), 2-bromo-5-methylpyridin-4-amine (200 mg, 1.069 mmol) and 2-(6-methylpyridin-2-yl)-6-phenyl-1,3,6,2-dioxazaborocane (287 mg, 1.017 mmol) were combined in DMF (5 mL) and heated at 105° C. for 2 days. The reaction mixture was then cooled and evaporated on a rotovap to give a residue which was purified by preparative HPLC eluting with a gradient of 5-30% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 30×75 mm column to afford the title compound as a yellow crystalline solid (44 mg). ESI-MS: m/z 200.2 (M+H).

Provenance & Evidence