(S)-3-fluoropyrrolidine → 5-Bromo-2-((S)-3-fluoro-pyrrolidin-1-yl)-nicotinonitrile

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Reaction Steps

5-Bromo-2-fluoro-nicotinonitrile (4) (5.0 g, 24.9 mmol) and (S)-(+)-3-fluoropyrrolidine (3.3 g, 25.9 mmol) were dissolved in dry MeCN (100 mL). TEA (8.0 mL, 57.4 mol) was added and the mixture stirred at rt for 2 hours. The solvent was evaporated in vacuo and the residue partitioned between H2O (100 mL) and EtOAc (100 mL). The organic phase was washed with saturated brine solution (100 mL), then dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was dissolved in DCM (100 mL) and the solvent evaporated in vacuo. The title compound was obtained as an off-white solid (6.3 g, 94%); LCMS, Rt=2.86 min (MeOH-FA method), m/z 270, 272 (MH+).

Provenance & Evidence