Heptane → 4-(4-Bromo-pyrazol-1-ylmethyl)-benzamide

Temperature

80 °C

A mixture of 4-bromo-1H-pyrazole (400 mg, 2.72 mmol), 4-(chloromethyl)benzamide (462 mg, 2.72 mmol), and potassium carbonate (940 mg, 6.80 mmol) in DMF (5 mL) was stirred for 2 hours at 80° C. The reaction mixture was then cooled to ambient temperature and diluted with diethyl ether (400 mL). The mixture was washed with water (2×100 mL) and brine (25 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was suspended in ethyl acetate (10 mL) and then diluted by the drop wise addition of n-heptane (40 mL). After stirring for 18 hours, the mixture was filtered and the collected solids were washed with n-heptane (3×10 mL). The collected solids were dried under reduced pressure to afford 4-((4-bromo-1H-pyrazol-1-yl)methyl)benzamide. MS ESI calcd. for C11H11BrN3O [M+H]+ 280 and 282. found 280 and 282. 1H NMR (500 MHz, DMSO-d6) δ 8.10 (s, 1H), 7.93 (s, 1H), 7.81 (d, J=8.5 Hz, 2H), 7.57 (s, 1H), 7.35 (s, 1H), 7.26 (d, J=8.0 Hz, 2H), 5.35 (s, 2H).

1. temperatureThe reaction mixture was then cooled to ambient temperature
2. washThe mixture was washed with water (2×100 mL) and brine (25 mL)
3. dry with materialThe organic layer was dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customto afford the crude product residue
7. stirringAfter stirring for 18 hours
8. filtrationthe mixture was filtered
9. washthe collected solids were washed with n-heptane (3×10 mL)
10. customThe collected solids were dried under reduced pressure

ORD record

ord-494bb98d78ee4bbeaddbd5477fcddb61

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242984B2