Lithium aluminum hydride → [2-Fluoro-6-(6-methoxy-pyridin-3-ylamino)-pyridin-3-yl]-methanol

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Reaction Steps

To 2-fluoro-6-(6-methoxy-pyridin-3-ylamino)-nicotinic acid methyl ester (54, 1.20 g, 4.33 mmol) in 50.0 mL of tetrahydrofuran, lithium tetrahydroaluminate (8.66 mL, 1.00 M in tetrahydrofuran, 8.66 mmol) is added and the reaction is stirred at room temperature for 3 hours. Sodium sulfate decahydrate (5 g) is added and after 1 hour, the reaction is filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (55, 700 mg). MS (ESI) [M+H+]+=250.1.

Provenance & Evidence