Isopropyl iodide → HCID 22497256, compound

Temperature

25 °C

A solution of 2,2,2-trifluoro-1-(6-fluoro-1H-indol-3-yl)-ethanone (1.63 g, 7.05 mmol) in N,N-dimethylformamide (15 mL) at 25° C. was treated with potassium carbonate (2.44 g, 17.63 mmol). The resulting mixture was stirred at 25° C. for 15 min. At this time, the reaction was treated with 2-iodopropane (1.06 mL, 10.58 mmol). The reaction was heated at 65° C. for 18 h. At this time, the reaction was cooled to 25° C. and was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was washed with a 1N aqueous hydrochloric acid solution (1×25 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 2/1 hexanes/ethyl acetate) afforded 2,2,2-trifluoro-1-(6-fluoro-1-isopropyl-1H-indol-3-yl)-ethanone (1.74 g, 90%) as a yellow solid: mp 67-69° C.; EI-HRMS m/e calcd for C13H11F4NO (M+) 273.0776, found 273.0780.

1. temperatureThe reaction was heated at 65° C. for 18 h
2. temperatureAt this time, the reaction was cooled to 25° C.
3. customwas partitioned between water (100 mL) and ethyl acetate (100 mL)
4. washThe organic layer was washed with a 1N aqueous hydrochloric acid solution (1×25 mL)
5. dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-26b208bc1b354d87a9d7705da02f5206

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06881844B2