Iodine → HCID 44544524, compound

Participants

Reaction Conditions

Reaction Steps

To (6-ethylsulfanylpyridin-3-yl)carbamic acid tert-butyl ester (27.6 g; 0.108 mol) and N,N,N′,N′-tetramethylethylenediamine (27 mL; 0.180 mol) in 300 mL diethyl ether at −78° C. was added dropwise n-butyllithium (100 mL of a 2.5 M solution in hexanes; 0.25 mol). The mixture was stirred mechanically for 15 minutes, warmed to 0° C.-5° C., stirred for 3 hours, cooled to −78° C. and iodine (60.6 g; 0.239 mol) in 300 mL of diethyl ether was added dropwise. The mixture was slowly warmed to room temperature, stirred overnight, and quenched with aqueous ammonium chloride and diethyl ether. The organic layer was washed with aqueous sodium metabisulfite, water, and brine, and dried over magnesium sulfate (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by CombiFlash chromatography using ethyl acetate and hexanes as the eluent. The product-rich fractions were concentrated in vacuo to provide (6-ethylsulfanyl-4-iodopyridin-3-yl)carbamic acid tert-butyl ester (27.7 g; 67%), MS (ES+) m/z 381 [M+H]+.

Provenance & Evidence