Potassium Carbonate → 2-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridine

Temperature

125 °C

To a mixture of 2,3-dichloropyridine (27.4 g, 185 mmol) and 3-bromopyrazole (i.e. the product of Step B) (25.4 g, 176 mmol) in dry N,N-dimethylformamide (88 mL) was added potassium carbonate (48.6 g, 352 mmol), and the reaction mixture was heated to 125° C. for 18 hours. The reaction mixture was cooled to room temperature and poured into ice water (800 mL). A precipitate formed. The precipitated solids were stirred for 1.5 hrs, filtered and washed with water (2×100 mL). The solid fiber cake was taken up in methylene chloride and washed separately with water, 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine. The organic extracts were then dried over magnesium sulfate and concentrated to afford 39.9 g of a pink sold. The crude solid was suspended in hexane and stirred vigorously for 1 hr. The solids were filtered, washed with hexane and dried to afford the title product as an off-white powder (30.4 g) determined to be >94% pure by NMR. This material was used without further purification in Step D.

1. temperatureThe reaction mixture was cooled to room temperature
2. customA precipitate formed
3. filtrationfiltered
4. washwashed with water (2×100 mL)
5. washwashed separately with water, 1 N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine
6. dry with materialThe organic extracts were then dried over magnesium sulfate
7. concentrationconcentrated
8. customto afford 39.9 g of
9. stirringstirred vigorously for 1 hr
10. filtrationThe solids were filtered
11. washwashed with hexane
12. customdried

ORD record

ord-70adb84df0e1465da898622212d1f4ce

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697734B2