Sodium Hydroxide → 2-Pyridinamine,3-fluoro-N-methyl-(9CI)

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Reaction Steps

(3-Fluoro-pyridin-2-yl)-methylamine dihydrochloride (1.313 g, 6.60 mmol) (WO 00/75134 A1; Chem. Pharm. Bull. 33:565, 1985) was partitioned between ether (6 mL) and 2.5 M NaOH (5 mL; 12.5 mmol). The aqueous layer (pH approx. 8) was extracted with DCM (4×20 mL). The aqueous layer was then brought to pH ˜12 with 2.5 M NaOH and extracted with DCM (2×20 mL), and the DCM and ether layers were combined, dried (2×Na2SO4), and concentrated under rotary evaporation at <30° C. to provide the free base of the title compound as a clear dark brown oil (780 mg, 94%). 1H-NMR (300 MHz, CDCl3) δ 8.38 (dt, 1H), 7.39-7.32 (m, 1H), 7.24-7.17 (m, 1H), 4.06 (d, 2H), 1.83 (br s, 2H).

Provenance & Evidence