Dimethylformamide → HCID 21345174, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-3-hydroxy-6-methylpyridine from Example 117c (Ig 7.87 mmole), 1-Cbz-2-(S)-azetidinemethyl tosylate (2.37 g 7.5 mmole, prepared as for example 105) and KOH (0.66 g 11.76 mmole) were combined in DMF (25 mL) and heated at 90° C. for one hour, cooled to 20° C. and poured into brine (100 mL). The resulting mixture was extracted with ether. The combined Et2O extracts were washed with 50% brine and dried (MgSO4). The solvent was evaporated under vacuum, and the crude product was chromatographed (silica gel; hexane/EtOAc 3:1) to yield 1.31 g (53%) of the title compound. 1H NMR (DMSO-d6, 120° C. 300 MHz) δ: 2.26 (m, 1H), 2.33 (s, 3H), 2.48 (m, 1H), 3.82-3.88 (m, 2H), 4.19 (q, J=3, 1H), 4.35 (q, J=4.5, 1H), 4.53 (m, 1H), 5.01 (s, 2H), 7.01 (d, J=8, 1H), 7.28 (m, 5H), 7.43 (m, 1H). MS (DCI/NH3) m/e 331 (M+H)+, 348 (M+NH4)+. Anal. calcd. for C18H19FN2O3 C, 65.44; H, 5.8; N, 8.48. Found: C, 65.04; H, 5.86; N, 8.44; [α]D −70.38 (c 1, MeOH).

Provenance & Evidence