Dimethylformamide → HCID 57749345, compound

To a mixture of 60% sodium hydride (212 mg, 5.31 mmol) and N,N-dimethylformamide (25 mL) was added with stirring at 0° C. ethyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate (1.00 g, 4.83 mmol), and the mixture was stirred at room temperature for 30 min. Iodoethane (581 μL, 7.24 mmol) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with water and extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, ethanol (4 mL) and 8N aqueous sodium hydroxide solution (2 mL) were added to the residue, and the mixture was stirred at room temperature for 2 hr and at 60° C. for 15 hr. The reaction mixture was neutralized with 1N hydrochloric acid, and the precipitated solid was collected by filtration and washed with water to give the title compound (710 mg, 71%) as a white solid.

1. additionwas added
2. stirringthe mixture was stirred at room temperature for 3 hr
3. extractionextracted with ethyl acetate
4. washthe organic layer was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltrated
7. concentrationThe filtrate was concentrated under reduced pressure, ethanol (4 mL) and 8N aqueous sodium hydroxide solution (2 mL)
8. additionwere added to the residue
9. stirringthe mixture was stirred at room temperature for 2 hr and at 60° C. for 15 hr
10. filtrationthe precipitated solid was collected by filtration
11. washwashed with water

ORD record

ord-4b46c6aed9934f08a3ddf1b0e24416c9

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304557B2