Sodium Carbonate → HCID 86625350, compound

Participants

Reaction Conditions

Reaction Steps

Benzo[b]thiophen-6-yl-carbamic acid tert-butyl ester (1.06 g, 4.30 mmol) is dissolved in THF (40 mL) and cooled to −78° C. Lithium diisopropylamine solution (8.5 mL of 2.0 M solution) and triisopropylborate (6.0 mL, 26 mmol) are added. The reaction is stirred at −78° C. for 90 minutes before the cooling bath is removed. After stirring for three hours, 2,4-dichloro-5-methylpyrimidine (0.74 g, 4.5 mmol), 1,1′-bis(diphenylphosphino) ferrocene (120 mg, 0.220 mmol), palladium (II) acetate (50.4 mg, 0.220 mmol), and sodium carbonate (9.5 mL of 2.0 N solution) are added. The reaction is heated at 70° C. for 20 hours. After the reaction solution is cooled to 25° C., water (100 mL) is added. The mixture is extracted with dichloromethane and the extracts are evaporated. The resulting solid is chromatographed on silica gel, eluting with EtOAc in hexanes 5-50%, to give the title compound as a yellow solid (0.32 g, 20% yield).

Provenance & Evidence