반응 #599929

반응 방정식

3-bromopyridine

N-(3-Chloro-1H-pyrazol-4-yl)acetamide

potassium carbonate

N,N′-dimethyethane-1,2-diamine

→

solid

수율 64.3%

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

수율 64.3%

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타to afford a solution
3. 3
   기타The mixture was purged with nitrogen three times
4. 4
   기타a major product formed
5. 5
   여과It was filtered through a pad of Celite®
6. 6
   세척the Celite® pad rinsed with acetonitrile (10 mL)
7. 7
   농축The combined filtrates were concentrated to about 5 mL and water (10 mL)
8. 8
   workup.ADDITIONwas added to the resulting suspension
9. 9
   workup.STIRRINGThe suspension was stirred for 1 hour
10. 10
    여과filtered
11. 11
    세척The solid was rinsed with water (2×5 mL)
12. 12
    기타dried under vacuum at room temperature

실험 절차

A 100-mL, 3-neck round bottom flask was charged with copper(I) chloride (59.6 mg, 0.602 mmol) and acetonitrile (10 mL), N,N′-dimethyethane-1,2-diamine (106 mg, 1.203 mmol) was added and the mixture was stirred under nitrogen to afford a solution. N-(3-Chloro-1H-pyrazol-4-yl)acetamide (480 mg, 3.01 mmol) and potassium carbonate (831 mg, 6.02 mmol) were added, followed by 3-bromopyridine (570 mg, 3.61 mmol). The mixture was purged with nitrogen three times and heated at 80° C. for 18 hours. Thin layer chromatography analysis [Eluent: ethyl acetate, SM Rf=0.5, Product Rf=0.3] indicated that a trace of starting material remained and a major product formed. It was filtered through a pad of Celite® and the Celite® pad rinsed with acetonitrile (10 mL). The combined filtrates were concentrated to about 5 mL and water (10 mL) was added to the resulting suspension. The suspension was stirred for 1 hour and filtered. The solid was rinsed with water (2×5 mL) and dried under vacuum at room temperature to afford a white solid (458 mg, 64%). Characterization matched sample prepared by previous method.

출처