Methyl iodide → 5-iodo-1,3-dimethylpyridin-2(1H)-one

Participants

Reaction Steps

To a stirred suspension of 5-iodo-3-methylpyridin-2-ol (Step 23.1) (1.67 g, 7.11 mmol) and K2CO3 (1.964 g, 14.21 mmol) in DMF (20 mL) was added MeI (0.666 mL, 10.66 mmol) at rt under Ar. The reaction mixture was stirred 1 hr at rt, concentrated, diluted with water, and extracted with EtOAc. The organic layers were combined and washed once with water, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 50-65) to afford the title product (1.40 g, 5.62 mmol, 79% yield) as a brown solid. tR: 3.31 min (HPLC 1); tR: 0.71 min (LC-MS 2); ESI-MS: 250 [M+H]+ (LC-MS 2); Rf=0.31 (hexane/EtOAc 1:1).

Provenance & Evidence