Sodium Carbonate → Ethyl 5-[4-(1-methylethyl)phenyl]pyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

4.68 g (20.32 mmol) of ethyl 5-bromonicotinate, 5.00 g (30.49 mmol) of 4-(1-methylethyl)-phenylboronic acid, 0.12 g (0.10 mmol) of tetrakis(triphenylphosphine)palladium(0) and 4.31 g (40.65 mmol) of sodium carbonate were dissolved in a mixture of 37 ml of 1,2-dimethoxyethane, 10.5 ml of water and 84 ml of dimethylformamide and stirred at 85° C. for 18 h. For work-up, some of the dimethylformamide was removed under reduced pressure, and the reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was dried over sodium sulphate and the crude product was purified by preparative HPLC. Yield: 2.42 g (44% of theory)

Provenance & Evidence