Potassium Carbonate → HCID 57603291, compound

Temperature

65 °C

To a solution of ethyl 6-chloro-5-methoxy-1-oxoindane-2-carboxylate (crude product from the preceding step, ˜141 mmol) in anhydrous dimethylacetamide (540 mL) was added K2CO3 (39 g, 282 mmol), KI (46.8 g, 282 mmol) and 1-bromo-2-fluoroethane (13.5 mL, 183 mmol) and the mixture was stirred and heated at 65° C. for 6 hours. The reaction mixture was diluted with THF (540 mL) and water (540 mL) and then cooled to 0° C. and treated with 5N aqueous NaOH (84 mL, 423 mmol). After 2 hours at 0° C., the reaction was quenched with 1N aqueous HCl (˜450 mL). Most of the THF was removed by rotary evaporation under reduced pressure and the aqueous residue was extracted with EtOAc. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered through a pad of silica gel and concentrated to give 6-chloro-2-(2-fluoroethyl)-5-methoxyindan-1-one.

1. temperaturecooled to 0° C.
2. customthe reaction was quenched with 1N aqueous HCl (˜450 mL)
3. customMost of the THF was removed by rotary evaporation under reduced pressure
4. extractionthe aqueous residue was extracted with EtOAc
5. washThe organic layer was washed with saturated NaHCO3
6. dry with materialdried over MgSO4
7. filtrationfiltered through a pad of silica gel
8. concentrationconcentrated

ORD record

ord-2e028ae9a6bd469b8d583865fb91d88c

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923568B2