Iodoethane → HCID 68511822, compound

Temperature

80 °C

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.

1. customThen it was quenched with a saturated aqueous NaHCO3 solution (20 ml)
2. extractionextracted with EE (3×60 ml)
3. washThe combined organic phases were washed with water
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated to small volume under vacuum
7. dissolutionThe residue (450 mg) was dissolved in DMF (6 ml)
8. temperatureThe reaction solution was then heated for 30 min at 50° C
9. extractionextracted with EE (3×80 ml)
10. washThe combined organic phases were washed with water and brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated to small volume under vacuum

ORD record

ord-03fcd3f7ede6434c8cdae0922109e6bf

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399673B2