Isopropyl iodide → HCID 66920857, compound

Participants

Reaction Conditions

Reaction Steps

6-Dimethoxymethyl-2-hydroxy-4-methylsulfanyl-nicotinonitrile sodium salt synthesized as described by Mahata, P. K. et al. Tetrahedron 59, 2003, 2631-2639 (3.5 g, 13.3 mmol) in 40 mL of anhydrous DMF was heated at 120° C. while 2-iodopropane (1.6 mL, 16.0 mmol) was added dropwise. The resulting mixture was heated at 120° C. for another 30 min before it was cooled to ambient temperature and partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, evaporated in vacuo. Purification on an Analogix MPLC system (SiO2 column) eluting with 10% EtOAc in hexanes yielded the titled compound as a light yellow solid upon standing (3.0 g, 80% yield).

Provenance & Evidence