Sodium Iodide → HCID 58790424, compound

Participants

Reaction Steps

The pyridinone 420 (0.283 g, 0.739 mmol), 2-chloro-N,N-dimethylethanamine (0.128 g, 0.887 mmol), cesium carbonate (0.547 g, 1.68 mmol) and sodium iodide (0.132 g, 0.88 mmol) were heated in DMF (10 mL) at 70° C. for 3 days. An additional portion of 2-chloro-N,N-dimethylethanamine (64 mg, 0.44 mmol) and cesium carbonate (0.289 g, 0.887 mmol) were added. The reaction mixture was heated for additional 8 hours, cooled to room temperature and evaporated under reduced pressure. The residue was partitioned between water (50 mL) and 5% ethanol/dichloromethane. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The residue was then purified by silica gel chromatography using a 25M Biotage column and a gradient of 3 to 20% methanol in dichloromethane with 1% acetic acid, to provide title compound 421 as a solid material (0.108 g, 32% yield). MS (m/z): 228.0 ([M+2H]/2), 455.0 (M+H), 477.0 (M+Na).

Provenance & Evidence