Isopropyl iodide → HCID 22497220, compound

Temperature

25 °C

A solution of 2,2,2-trifluoro-1-(6-methoxy-1H-indol-3-yl)-ethanone (1.0 g, 4.11 mmol) in N,N-dimethylformamide (10 mL) at 25° C. was treated with potassium carbonate (1.42 mg, 10.28 mmol). The resulting mixture was stirred at 25° C. for 30 min and then was treated with 2-iodopropane (0.62 mL, 6.17 mmol). The reaction was heated at 65° C. for 20 h. At this time, the reaction was cooled to 25° C. and was partitioned between water (50 mL) and ethyl acetate (50 mL). This mixture was treated with a 1N aqueous hydrochloric acid solution (25 mL), shaken, and separated. The organic layer was washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 3/1 hexanes/ethyl acetate) afforded 2,2,2-trifluoro-1-(1-isopropyl-6-methoxy-1H-indol-3-yl)-ethanone (99 mg, 85%) as a yellow solid: mp 58-60° C.; EI-HRMS m/e calcd for C14H14F3NO2 (M+) 285.0977, found 285.0974.

1. temperatureThe reaction was heated at 65° C. for 20 h
2. temperatureAt this time, the reaction was cooled to 25° C.
3. customwas partitioned between water (50 mL) and ethyl acetate (50 mL)
4. additionThis mixture was treated with a 1N aqueous hydrochloric acid solution (25 mL)
5. stirringshaken
6. customseparated
7. washThe organic layer was washed with water (1×50 mL)
8. dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-06ee2bf974a54e669a20bb280c9386d1

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06881844B2