Trimethylsilyldiazomethane → 2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid

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Reaction Steps

2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid (1.17 g, 5.05 mmol) was dissolved in a mixture of DCM (20 mL) and MeOH (5 mL) and treated with (trimethylsilyl)diazomethane (2.0 m in diethyl ether, 5.0 mL, 10.00 mmol). [2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid was synthesized according to M. Schlosser and T. Rausis, Eur. J. Org. Chem., 2004, pp 1018-1024]. The derived solution was maintained at rt for 1 hour. Evaporation under reduced pressure and purification using the by silica gel chromatography (hexane to ethyl actetate gradient) gave the desired methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate.

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