Sodium Formate → HCID 58949905, compound

Participants

Reaction Steps

A 3-neck flask equipped with a condenser and 2 septa was flushed with N2, then the flask was charged with 0.6 g (2.7 mmol) 3-(3-bromophenyl)-2-methylpropionitrile (9-2), 0.275 g (4 mmol) sodium formate, 0.155 g (0.13 mmol) tetrakis(triphenylphosphine)Palladium and flushed with CO from a balloon for 5 min. The solids were suspended in 10 mL DMF and CO continued to bubble into the liquid. The flask was heated in an oil bath at 100′ for 20 min then 110′ while stirring. The color changed from yellow to a deep orange color after 1.5 h, and HPLC/MS analysis showed no starting material and one major product. The reaction was cooled and quenched with brine. The product was extracted into EtOAc, dried over Na2SO4, filtered and concentrated. The product was dissolved in 1 mL CH2Cl2 and purified on an Isco automated system affixed with a Biotage Flash 25(M) cartridge eluted with 0-50% EtOAc in hexane at 25 mL/min over 15 min and hold for 30 min. The product eluted last. MS 174.1 NB#212867-104

Provenance & Evidence