Iodoethane → HCID 68511822, compound

Participants

Reaction Conditions

Reaction Steps

3.4 g (8.2 mmol) Lawesson's reagent were added at RT to a solution of 550 mg (2.1 mmol) 6,7-difluoro-2-hydroxy-4-methyl-quinoline-3-carboxylic acid ethyl ester in a pyridine/toluene blend (1:10 vv, 6 ml) and then the mixture was heated for 3 h at 80° C. Then it was quenched with a saturated aqueous NaHCO3 solution (20 ml) and extracted with EE (3×60 ml). The combined organic phases were washed with water, dried over Na2SO4, filtered and concentrated to small volume under vacuum. The residue (450 mg) was dissolved in DMF (6 ml) and mixed with 660 mg (4.8 mmol) K2CO3 and 740 mg (4.8 mmol) iodoethane. The reaction solution was then heated for 30 min at 50° C. It was then diluted with water (60 ml) and extracted with EE (3×80 ml). The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 19:1) of the residue yielded 300 mg (0.96 mmol, 47%) 2-ethylsulfanyl-6,7-difluoro-4-methyl-quinoline-3-carboxylic acid ethyl ester.

Provenance & Evidence