Sodium Carbonate → HCID 22462549, compound

Participants

Reaction Steps

A stirred mixture of 3-bromo-5-nitrobenzo[b]thiophene (J.Amer. Chem. Soc, 1948, 1955) (4.2 g, 0.016 mole,) pyridin-4-ylboronic acid (2.0 g, 0.016 mole) and sodium carbonate (4.3 g, 0.048 mole) in DME (150 ml) and water (150 ml) was de-gassed by bubbling argon through for 15 minutes, then tetrakis(triphenylphosphine)palladium (0) (400 mg) was added and the mixture heated at reflux under argon for 18 hours. The reaction mixture was cooled and concentrated in vacuo to approx 150 ml volume, then acidified with 2M HCl acid (200 ml) and shaken well with ethyl acetate (400 ml). The solid present was filtered off, shaken with 10% Na2CO3 solution and dichloromethane, and the organic layer separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound as an orange/yellow solid (2.3 g, 56%).

Provenance & Evidence