Aluminium lithium hydride → HCID 57963218, compound

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Reaction Steps

To 2-fluoro-6-(4-methoxy-benzylamino)-nicotinic acid methyl ester (43, 70 g, 241 mmol) in 350 mL of tetrahydrofuran, lithium aluminum hydride (362 mL, 1 M in tetrahydrofuran, 362 mmol) is added dropwise while cooling. The reaction is stirred at room temperature for 2 hours, then quenched with dropwise addition of 14 mL of water, 14 mL of 15% aqueous sodium hydroxide, and 42 mL of water, sequentially. Then 500 mL of methyl tert-butyl ether is added and solids are removed by filtration. The filtrate is concentrated under vacuum and the resulting solid is dissolved in dichloromethane, passed through a plug of silica gel and eluted with 50-100% ethyl acetate in heptane. The solvent is removed under vacuum to provide the desired compound as an off-white solid (44, 63 g, 240 mmol, 100% yield).

Provenance & Evidence