Dimethylformamide → HCID 53946632, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 ml round bottomed flask with stirring bar and an argon inlet was added Pd(OAc)2 (0.036 g, 0.15 mmol), bisdiphenylphosphinoferrocene (DPPF, 0.12 g, 0.2 mmol), and 15 ml of DMF were heated to 50° for 15 minutes. Cooled the reaction to room temperature then added 2-iodo-3-methyl-pyrazine (1.2 g, 5.4 mmol)(5). (a prep from Albert Hirschberg et al. J.Org. Chem. Jun.,1961 p1907-1912) and 4-formylbenzenboronic acid (0.90 g, 6.0 mmol) and Et3N (1.05 ml, 7.5 mmol). The mixture was heated to 90° C. for 10 h. Removed solvent in vacuo, taken up with CHCl3 and washed with diluted NH4OH. The organic layer was dried (MgSO4), filtered and concentrated to yield a black oil. This material was chromatographed (silica gel, 30% EtOAc/Hexane) to afford the title product.

Provenance & Evidence