Potassium Carbonate → tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

2-Bromo-3-methylpyridine (50.0 g, 291 mmol), 3-(tert-butoxycarbonyl)phenyl-boronic acid (68.4 g, 308 mmol), potassium carbonate (96.4 g, 697 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (Pd(dppf)Cl2, 3.19 g, 3.91 mmol) were dissolved in a mixture of 1.5 L of toluene and 350 mL of water. The resulting solution was stirred and heated at 80° C. for 16 hours. The reaction mixture was cooled to 25° C. and then the layers were separated. The organic layer was evaporated to dryness and was then purified on 3 kg of silica gel utilizing a gradient of 0-18.5% ethylacetate in hexanes to yield tert-butyl 3-(3-methylpyridin-2-yl)benzoate as a pale yellow oil (49.3 g, 63%). ESI-MS m/z calc. 269.1. found 270.2 (M+1)+. Retention time 0.93 minutes

Provenance & Evidence