1H-Indazole → HCID 59743345, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1H-indazole (2.36 g, 20.0 mmol) in anhydrous DMF (100 mL) was treated with NaH (60% dispersion in mineral oil, 1.60 g, 40.0 mmol) at RT for 10 min. 4-Chloro-2-methylthiopyrimidine (2.55 ml, 22.0 mmol) was then added in one portion at RT, and the resulting mixture stirred at 70° C. for 2.5 h. The reaction mixture was cooled to RT, quenched with aqueous HCl (1 M), and extracted with EtOAc. The layers were separated, the organic layer washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was absorbed onto silica gel and purified by flash chromatography (ethyl acetate/hexane, gradient from 5:95 to 25:75) to afford a mixture of 1-(2-methyl-sulfanyl-pyrimidin-4-yl)-H-indazole and 2-(2-methylsulfanyl-pyrimidin-4-yl)-2H-indazole (3.77 g, 78% yield) as a beige solid.

Provenance & Evidence