HCID 118022928, compound → 3-(3-chloro-1H-pyrazol-1-yl)pyridine

Temperature

85 °C

To a solution of 3-(3-chloro-4,5-dihydro-1H-pyrazol-1-yl)pyridine (1.09 g, 6.00 mmol) in dry N,N-dimethylformamide (6.0 mL) in a 25 mL round bottom flask was added copper(I) chloride (0.178 g, 1.80 mmol) leading to a green suspension. Dried air was bubbled through the mixture. The resultant dark green mixture was stirred at 85° C. for 16 hours. The mixture was then cooled down and dispersed into water (20 mL) and ethyl acetate (20 mL). The mixture was filtered through a pad of Celite® and washed thoroughly with ethyl acetate (4×20 mL). Aqueous layer was extracted with ethyl acetate (4×20 mL). The combined organic extracts were dried over anhydrous sodium sulfate (Na2SO4) and concentrated to afford crude product (0.582 g, 51%).

1. customDried air
2. customwas bubbled through the mixture
3. temperatureThe mixture was then cooled down
4. additiondispersed into water (20 mL) and ethyl acetate (20 mL)
5. filtrationThe mixture was filtered through a pad of Celite®
6. washwashed thoroughly with ethyl acetate (4×20 mL)
7. extractionAqueous layer was extracted with ethyl acetate (4×20 mL)
8. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate (Na2SO4)
9. concentrationconcentrated

ORD record

ord-27490bed1aa9401899f2f2ea1cf9b9b5

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108946B2