2-Propanethiol → 5-iso-Propylthiomethyl-pyridine-2-carbonitrile

Participants

Reaction Steps

Add 2-propanethiol (0.53 mL, 5.6 mmol) to a slurry of 5-bromomethyl-pyridine-2-carbonitrile (1.1 g, 5.6 mmol) and cesium carbonate (1.8 g, 5.6 mmol) in DMF (10 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 16 h at room temperature. Dilute the mixture with hexane/EtOAc (1:1, 100 mL) and wash with 5% aqueous NaCl (3×30 mL). Collect the organic phase, concentrate in vacuo and purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (20:1 to 7:3 gradient) to obtain the desired intermediate (0.83 g, 77%). MS (ES+) m/z: 193.2 (M+H)+.

Provenance & Evidence