Isopropyl iodide → HCID 22497243, compound

Temperature

25 °C

A solution of 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone (1.0 g, 3.87 mmol) in N,N-dimethylformamide (10 mL) at 25° C. was treated with potassium carbonate (1.34 g, 9.68 mmol). The resulting mixture was stirred at 25° C. for 10 min and then treated with 2-iodopropane (0.58 mL, 5.81 mmol). The reaction was heated at 65° C. for 3 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). 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 to afford 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (581 mg, 98%) as a yellow solid: mp 143-145° C.; EI-HRMS m/e calcd for C14H14F3NO (M+) 269.1027, found 269.1037.

1. temperatureThe reaction was heated at 65° C. for 3 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. washThe organic layer was washed with water (1×50 mL)
6. dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-6793ae21d9d04abe938b36368e88f452

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06881844B2