Sodium Carbonate → HCID 90389413, compound

Participants

Reaction Conditions

Reaction Steps

A microwave glass vessel was charged with 3-bromo-5-chloropicolinonitrile (0.5 g, 2.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.115 mmol) and sodium carbonate (0.731 g, 6.90 mmol). The vial was evacuated and back-filled with nitrogen. Dioxane (10 mL) and water (3 mL) were added. The reaction mixture was degassed and isopropenylboronic acid pinacol ester (0.474 ml, 2.53 mmol) was added. The reaction mixture was heated to 90° C. for 2 hs. The reaction mixture was partitioned between water and EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in EtOH (7 mL) and NaOH (5M, 3 mL). The solution was heated to 115° C. for 1.5 hrs. The reaction mixture was partitioned between water and EtOAc. The organic phase was discarded and the aq. phase was acidified with aq. 2 M HCl and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated under reduced pressure to obtain the title compound as a light-yellow solid (0.373 g, 82%). MS m/z=198.1 [M+H]+. Calculated for C9H8ClNO2: 197.024

Provenance & Evidence