Iodine → [1-(6-Chloro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

Add tert-butyllithium (35 mL, 59.6 mmol) to a solution of [1-(6-chloro-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (5.1 g, 19.87 mmol) in THF (60 mL) under N2 at −78° C. After 30 min, add iodine (7.6 g, 29.8 mmol) in THF (20 mL) over 30 min at −78° C. Stir for 1 hour and then warm up to room temperature. Quench with water, extract in ethyl acetate with saturated aqueous sodium chloride, dry over Na2SO4. Purify on column chromatography 5% to 20% ethyl acetate in hexanes to obtain product (1 g). MS (ES) m/z 383 [M+1]+.

Provenance & Evidence