반응 #599901

반응 방정식

N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide

tetrahydrofuran

Sodium tert-butoxide

ethyl bromide

→

solid

수율 89.0%

N-(3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylacetamide

수율 89.0%

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   기타the reactor was capped with a septa
2. 2
   농축The mixture was concentrated
3. 3
   기타to give a brown residue, which
4. 4
   추출The aqueous layer was extracted with ethyl acetate (2×20 mL)
5. 5
   농축the combined organics were concentrated to dryness
6. 6
   세척eluted with ethyl acetate (200 mL)
7. 7
   농축The filtrates were concentrated to dryness
8. 8
   기타further dried under vacuum at 20° C.

실험 절차

To a 3-neck, 100-mL round bottom flask was charged N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1.66 g, 7.0 mmol) and tetrahydrofuran (16 mL). Sodium tert-butoxide (0.843 g, 8.77 mmol, 1.25 eq) and ethyl bromide (0.78 mL, 10.52 mmol, 1.5 eq) were added and the reactor was capped with a septa. The reaction was stirred at 58° C. for 24 hours, at which point HPLC analysis indicated that only 1.97% starting material remained. The mixture was concentrated to give a brown residue, which was dissolved in water (20 mL) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organics were concentrated to dryness. The residue was passed through a silica gel plug (40 g silica) and eluted with ethyl acetate (200 mL). The filtrates were concentrated to dryness and further dried under vacuum at 20° C. to afford a yellow solid (1.68 g, 89%). Characterization matched sample prepared by previous method.

출처