Sodium Carbonate → 2-Fluoro-3-(2-methylpyridin-4-yl)pyridine

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Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-methylpyridine (25.0 g, 145 mmol), 2-fluoropyridin-3-ylboronic acid (22.5 g, 160 mmol), Pd(PPh3)2Cl2 (5.10 g, 7.27 mmol), and sodium carbonate (46.2 g, 436 mmol) in 1,2-dimethoxyethane:ethanol:water (7:2:0.75, 292.5 ml total volume) was heated to 80° C. for 4 h. After cooling to room temperature, the mixture was diluted with saturated aqueous sodium bicarbonate solution and water, then extracted with dichloromethane (3×). The combined organic extracts were then extracted with 2 N aqueous HCl solution (4×). The combined aqueous layers were washed with dichloromethane, then the pH was raised to 10 with 10 N NaOH. The resulting suspension was extracted with dichloromethane (3×). The combined extracts were concentrated in vacuo to give 2-fluoro-3-(2-methylpyridin-4-yl)pyridine (22.14 g, 118 mmol, 81% yield).

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