Pyridine → HCID 18456834, compound

Participants

Reaction Steps

To a flask was charged with 3-hydroxy-4-methylphenylacetonitrile (32a; 0.92 g; 6.2 mmol), Cu(OAc)2 (1.3 g; 6.9 mmol), 3-bromobenzeneboronic acid (1.1 g; 5.5 mmol) and powdered 4 Å molecular sieves, was added CH2Cl2 (62 mL) followed by pyridine (2.5 mL; 31 mmol). The reaction was stirred at rt for 3 days. The suspension was filtered through a bed of CELITE®/silica gel and the solid washed with CH2Cl2. The combined filtrates were washed sequentially with 2N HCl (2×25 mL), NaHCO3 (25 mL), water and brine. The extracts were dried (MgSO4), filtered and evaporated. The crude product 76 was sufficiently pure to use in the next step.

Provenance & Evidence