Sodium Carbonate → 5-(4-Chlorophenyl)-2-methylpyridine

Participants

Reaction Steps

The trifluoromethane sulfonate from Step 1 (500 mg) was dissolved in 10 mL of toluene, 5 mL of EtOH, and 1.6 mL of 2M aqueous Na2CO3. Then 203 mg LiCl, 411 mg of 4-chlorobenzeneboronic acid (Lancaster) and 832 mg of tetrakis (triphenylphosphine) palladium were added successively. The resulting reaction mixture was heated up to 90°-95° C. for 1 hour. The reaction mixture was cooled down to room temperature, EtOAc was added, and the organic phase was washed with 1N NaOH, brine, dried over MgSO4, filtered, and concentrated. Purification by flash chromatography using hexane: EtOAc 3:2 gave the title compound.

Provenance & Evidence