Iodine → N-(3-Iodopyridin-2-yl)-2,2-dimethylpropanamide

Participants

Reaction Conditions

Reaction Steps

N-(pyridin-2-yl)pivalamide (14.25 g, 80 mmole) and TMEDA (29.80 ml, 200 mmole) were dissolved in THF (400 ml) under nitrogen and n-BuLi (125 ml, 200 mmole; 1.6 M solution in n-hexane) was added dropwise at −75° C. The mixture was stirred for 15 minutes at −75° C. and then for 2 hours at −10° C. After renewed cooling to −75° C. a solution of iodine (50.76 g, 200 mmole) in THF (200 ml) was added dropwise and the reaction mixture was stirred for 2 hours. The mixture was heated to 0° C. and quenched with saturated aqueous sodium thiosulfate solution. The aqueous phase was extracted with DCM (2×150 ml) and the combined organic phases were dried over MgSO4. After filtering off the drying agent and removing the solvent on a rotary evaporator, the residue was purified by column chromatography (ether: cyclohexane=3:1) and N-(3-iodopyridin-2-yl)pivalamide (14.80 g, 61%) was thereby obtained.

Provenance & Evidence