1,2-Diiodoethane → HCID 178434246, compound

Participants

Reaction Conditions

Reaction Steps

To a 150 mL round-bottomed flask was added 3-methyl-5-(oxazol-5-yl)-1H-indazole (0.90 g, 4.52 mmol), and THF (20 mL). The resulting reaction mixture was stirred at −78° C. The solution was then treated dropwise via syringe with lithium bis(trimethylsilyl)amide (1.0 M solution in THF (13.6 mL, 13.6 mmol)), and the reaction was stirred for 1 hour at −78° C. A THF solution of 1,2-diiodoethane (5.20 mmol) was then added dropwise and the reaction was allowed to warm to room temperature for 1 hour. The reaction was then poured into a 1:1 mixture of ether and saturated sodium thiosulfate. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 10 to 50% EtOAc in Hexanes to give the desired product as a tan powder (1.01 g, 69% yield). LCMS (API-ES) m/z (%): 325 (100%, M++H).

Provenance & Evidence