Sodium Bicarbonate → HCID 69589156, compound

27.6 ml (27.6 mmol) of a 1M solution of diisobutylaluminum hydride in dichloromethane were added dropwise to a solution of 3.88 g (12.5 mmol) of ethyl 3-[2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrol-4-yl]acrylate in 120 ml of dichloromethane at −78° C. with stirring. The resulting mixture was stirred at the same temperature for 3 hours. At the end of this time, the reaction mixture was added to a saturated aqueous solution of sodium hydrogencarbonate and the resulting mixture was filtered. The filtrate was extracted with dichloromethane and the organic extract was washed with water, dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 9:1 by volume mixture of hexane and ethyl acetate as the eluant to afford 3.42 g (yield 93%) of the title compound as a pale brown powder.

1. stirringThe resulting mixture was stirred at the same temperature for 3 hours
2. filtrationthe resulting mixture was filtered
3. extractionThe filtrate was extracted with dichloromethane
4. extractionthe organic extract
5. washwas washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated by evaporation under reduced pressure
8. customThe residue thus obtained
9. customwas purified by chromatography on a silica gel column
10. additionby volume mixture of hexane and ethyl acetate as the eluant

ORD record

ord-cd6b98fb726343eca548426a6bc510ea

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122666B2