1H-1,2,4-Triazole → HCID 68770387, compound

Temperature

50 °C

A mixture of 2,6-difluoro-benzonitrile (10.34 g, 74.4 mmol), 1H-[1,2,4]triazole (5.34 g, 77.4 mmol), and CsCO3 (25.19 g, 77.4 mmol) in DMSO (30 mL) was stirred at ˜50° C. for 24 h. The yellowish easily stirred slurry was then diluted with water (200 mL), stirred at rt for 15 min, and filtered. The filter cake was washed with water (1×100 mL) and the filter cake was then partitioned with water (100 mL) and DCM (200 mL). The aqueous layer was extracted with DCM (1×300 mL), and the organic layers were combined, washed with 4 M NaCl (1×100 mL), dried (Na2SO4), and concentrated under vacuum at 90° C. to provide the crude title compound as an off-white solid (8.96 g). A portion of this crude material (3.33 g) was dissolved in DCM/MeOH, silica gel (8.5 g) was added, and the mixture was concentrated to a free-flowing powder. The silica-adsorbed crude title compound was applied to a silica flash column (40 mm×6″) and eluted with EtOAc to afford the title compound as a white solid [1.60 g, 31% (calculated from chromatographic purification of a portion of the crude material)].

1. stirringstirred at rt for 15 min
2. filtrationfiltered
3. washThe filter cake was washed with water (1×100 mL)
4. customthe filter cake was then partitioned with water (100 mL) and DCM (200 mL)
5. extractionThe aqueous layer was extracted with DCM (1×300 mL)
6. washwashed with 4 M NaCl (1×100 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under vacuum at 90° C.
9. customto provide the crude title compound as an off-white solid (8.96 g)
10. additionsilica gel (8.5 g) was added
11. concentrationthe mixture was concentrated to a free-flowing powder
12. washeluted with EtOAc

ORD record

ord-cd974fcc38144de596fffb5c65638a4e

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829584B2