C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[C:13]([O:19][CH3:20])=[N:14][CH:15]=[C:16]([F:18])[CH:17]=2)=[N:6][CH:5]=1.[AlH4-].[Li+].[OH-].[Na+].Cl>O1CCCC1>[F:18][C:16]1[CH:17]=[C:12]([CH2:11][NH:10][C:7]2[N:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)[C:13]([O:19][CH3:20])=[N:14][CH:15]=1
To 6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-nicotinic acid methyl ester (91, 0.825 g, 2.83 mmol) in 11 mL of tetrahydrofuran, lithium tetrahydroaluminate (5.66 mL, 1.0 M in tetrahydrofuran, 5.66 mmol) was added at −40° C. under nitrogen. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was poured into aqueous 1M sodium hydroxide, then neutralized with aqueous 1M hydrochloric acid. The solids were filtered out through celite, the celite washed with ethyl acetate and tetrahydrofuran. The isolated aqueous layer was extracted with ethyl acetate and all organic layers were combined, washed with brine, then dried over sodium sulfate, filtered and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (92, 357 mg). MS (ESI) [M+H+]+=264.4.
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