Imidazole → HCID 58585766, compound

Participants

Reaction Steps

To the solution of 4-(3-hydroxy-propylsulfanyl)-6-iodo-quinoline-3-carbonitrile (example 50a, 3.0 g, 8.1 mmol) and imidazole (2.2 g, 32.4 mmol) in DMF (10 mL) was added dropwisely the solution of tert-butyldimethylsilyl chloride (TBDMS-Cl, 2.94 g, 19.4 mmol) in DMF (10 mL). The reaction mixture was stirred at room temperature overnight. The product was extracted with ethylacetate. The combined organic layers were successively washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 5%-30% ethyl acetate in hexanes in 50 min) afforded 4-[3-(tert-butyl-dimethyl-silanyloxy)-propylsulfanyl]-6-iodo-quinoline-3-carbonitrile (3.41 g, 87%) as a yellow solid. LC-MS m/e 485 (MH+).

Provenance & Evidence