Potassium Carbonate → 2-Chloro-4-(3-fluoro-4-methyl-phenyl)-pyridine

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Reaction Steps

To a vial was added 2-chloro-4-bromopyridine (96 mg, 0.5 mmol), Pd(PPh3)4 (30 mg), and toluene/EtOH (4:1, 3 mL). After stirring at room temperature for 5 min, 3-fluoro-4-methylphenylboronic acid (115 mg, 0.75 mmol) and 2 M aqueous K2CO3 (1 mL) were added, and the resulting mixture was heated at 90° C. for 16 h. The resulting mixture was poured into water and extracted with EtOAc. The organic layer was dried and concentrated, and the residue was purified by preparative TLC (hexanes/EtOAc) to yield 2-chloro-4-(3-fluoro-4-methyl-phenyl)-pyridine as a solid.

Provenance & Evidence