Hydrochloric Acid → HCID 71735040, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[(6-chloro-3-pyridyl)methyl]-2-methylsulfanyl-imidazo[4,5-b]pyridine (2.22 g, 7.63 mmol) in 25 mL concentrated aqueous hydrochloric acid was cooled to −10° C. and gaseous Cl2 was bubbled through the solution for 1 h. The mixture was stirred at −10° C. for additional 2 h and for 12 h at room temperature. Afterwards the reaction mixture was poured into ice-water, basified to pH 4-5 with NaOH solution (15% in H2O) and extracted three times with CH2Cl2. The combined organic extracts were washed with water, dried with Na2SO4 and the solvent was removed under reduced pressure. Purification by flash column chromatography (SiO2, gradient of MeOH/CH2C12) yielded 1.23 g (4.43 mmol, 58%) of compound E1.8.

Provenance & Evidence