Methanol → Methyl 6-chloro-2-methoxynicotinate

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Reaction Steps

Methyl 6-chloro-2-fluoronicotinate (Example 454, Step 1) (76 mg, 0.40 mmol) was taken up in a 0.5 M solution of sodium methoxide in methanol (0.80 ml, 0.40 mmol) and stirred at room temperature for 3 hours. The mixture was quenched with saturated aqueous ammonium chloride and extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-17% ethyl acetate/hexanes) to afford the title compound as a white solid.

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