Potassium Carbonate → 3-Methoxy-6-methyl-2-(3-trifluoromethylphenyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

To the 2-bromo-3-methoxy-6-methyl-pyridine synthesized above (1.2 g, 5.94 mmol), 3-trifluoromethylphenylboronic acid (1.69 g, 8.91 mmol), PPh3 (0.31 g, 1.19 mmol), K2CO3 (2.46 g, 17.82 mmol) and Pd(OAc)2 (0.13 g, 0.59 mmol) was added DME (15 mL), and EtOH—H2O (1:1, 6 mL). Ar gas was bubbled through the stirred reaction for 5 min. The reaction was stirred at 80° C. under Ar for 20 h. The reaction was cooled to room temperature, concentrated, and H2O and dichloromethane (40 mL each) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic extracts were dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 1:1 dichloromethane-hexanes then dichloromethane to afford 1.36 g (86%) of 3-methoxy-6-methyl-2-(3-trifluoromethyl-phenyl)-pyridine (I-4, Y═R1═CH3, R2═CF3) as a light yellow solid.

Provenance & Evidence