Benzimidazole → HCID 86695314, compound

Temperature

110 °C

0.16 g (0.836 mmol) of CuI, 1.20 g (10.15 mmol) of benzimidazole and 5.70 g (17.50 mmol) of cesium carbonate (CeCO3) were successively added into a 50 ml round bottom flask wrapped by aluminum foil, after introducing nitrogen for 15 minutes, 1 mL (8.36 mmol) of 2,4-difluoro-iodobenzene, 0.30 g (1.67 mmol) of 1,10-ortho-phenanthroline and 25 mL of anhydrous N,N-dimethylformamide (DMF) were successively added to the nitrogen stream to form a reaction mixture; after 30 minutes of continually introducing nitrogen to the reaction mixture, the system was heated in oil bath to 110° C. and stirred for 24 hours; after the reaction was cooled to room temperature, it was concentrated in vacuum, and 10 mL of ethyl acetate was added to the concentrate, the precipitate was removed by filtering, the concentrate was then washed with 30 mL of ethyl acetate, the filtrate was concentrated; the filtrate was applied to silica gel column chromatography using a mixture solution containing ethyl acetate and n-hexane in a volume ratio of 2:3 as eluant, and 0.942 g of 1-(2,4-difluorophenyl)-benzimidazole in a form of yellow liquid was obtained with the yield of 48%.

1. additionafter introducing nitrogen for 15 minutes
2. customto form a reaction mixture
3. temperatureafter the reaction was cooled to room temperature
4. concentrationit was concentrated in vacuum, and 10 mL of ethyl acetate
5. additionwas added to the concentrate
6. customthe precipitate was removed
7. filtrationby filtering
8. washthe concentrate was then washed with 30 mL of ethyl acetate
9. concentrationthe filtrate was concentrated
10. additioncontaining ethyl acetate and n-hexane in a volume ratio of 2:3 as eluant

ORD record

ord-269e73cd557742a8ab7d1fb6e55ee9a7

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09159936B2