[F:1][C:2]1[C:3]([CH3:11])=[N:4][CH:5]=[C:6]([CH:10]=1)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.C([N:32]([CH2:36]C)C(C)C)(C)C.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1>[CH2:38]([O:45][C:36](=[O:19])[NH:32][C:6]1[CH:5]=[N:4][C:3]([CH3:11])=[C:2]([F:1])[CH:10]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1To a solution of 5-fluoro-6-methyl-nicotinic acid (0.17 g, 1.10 mmol) in toluene (10 mL) is added diphenylphosphoryl azide (0.30 mL, 1.3 mmol) followed by N,N-diisopropylethylamine (0.21 mL, 1.20 mmol). The mixture is stirred at room temperature for 1 h then benzyl alcohol (0.14 mL, 1.30 mmol) is added and the reaction mixture is heated to 110° C. for 2 h. The mixture is cooled to room temperature and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography using a 0-30% gradient of EtOAc/heptanes to provide 0.196 g of (5-fluoro-6-methyl-pyridin-3-yl)-carbamic acid benzyl ester as a solid.
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