Iodine → 7-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

(2-Chloro-4-iodo-6-trifluoromethyl-pyridin-3-yl)-carbamic acid methyl ester: sec-Butyllithium solution (1.3 M in cyclohexane, 7.55 mL, 5.81 mmol) was added at −78° C. to a solution of (2-chloro-6-trifluoromethyl-pyridin-3-yl)-carbamic acid methyl ester (1.00 g, 3.93 mmol) and N,N,N′,N′-tetramethylethylenediamine (1.14 g, 9.82 mmol) in THF (50 mL). The solution was stirred for 1 h at −10° C., then cooled again to −78° C. and treated with a solution of iodine (1.66 g, 6.52 mmol) in THF (20 mL). After stirring for 1 h at −10° C., the reaction mixture was partitioned between ethyl acetate and 30% aq. sodium sulfite solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography of the residue (SiO2, dichloromethane) afforded the title compound (810 mg, 54%). White solid, MS (EI) 345.0 (100), 379.9 (2, M+).

Provenance & Evidence