Sodium Carbonate → [2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]acetonitrile

Participants

Reaction Steps

To a solution of (4-bromo-2-methylphenyl)acetonitrile (1 eq.) and [2-(3-methoxypropyl)phenyl]boronic acid from EXAMPLE 3 step 1, in DMF (0.22M) was added aqueous Na2CO3 (2M; 3 eq.). Nitrogen was bubbled in the solution for 15 min before the addition of PdCl2(dppf)2 (0.05 eq.). The final mixture was stirred at 90° C. for 12 h, cooled to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water, HCl (0.01M), brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (5 to 30% in 30 min) afforded the desired compound as a colorless oil.

Provenance & Evidence