Dimethylformamide → 1-(2-isopropoxy-ethyl)-3-nitro-1H-pyrazole

Temperature

25 °C

In a round bottom flask was placed 3-nitro-1H-pyrazole (prepared in example 3, 315 mg, 2.79 mmol) and dry N,N-dimethylformamide (5 mL). This solution was then treated with sodium hydride (95%, 80 mg, 3.35 mmol) and gas evolution occurred. It was then stirred another 15 min at 25° C. 2-(2-Iodo-ethoxy)-propane (896 mg, 4.18 mmol) was then added to the reaction mixture and the reaction was stirred at 25° C. for 6 h. The reaction was then diluted with ethyl acetate (10 mL) and washed with water (2×10 mL). The aqueous layers were then combined and extracted with ethyl acetate (2×10 mL). The organic layers were combined and washed with a saturated aqueous brine solution (10 mL) and then dried over sodium sulfate, filtered and concentrated in vacuo. Purification on an AnaLogix Intelliflash system (12 g column, 25% ethyl acetate/hexanes to 35% ethyl acetate/hexanes) afforded 1-(2-isopropoxy-ethyl)-3-nitro-1H-pyrazole (428 mg, 77%) as a light yellow oil.

1. customIn a round bottom flask was placed
2. stirringthe reaction was stirred at 25° C. for 6 h
3. washwashed with water (2×10 mL)
4. extractionextracted with ethyl acetate (2×10 mL)
5. washwashed with a saturated aqueous brine solution (10 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification on an AnaLogix Intelliflash system (12 g column, 25% ethyl acetate/hexanes to 35% ethyl acetate/hexanes)

ORD record

ord-3d70759928064226bed2964033426683

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935699B2