Triethylborane → HCID 9908822, compound

To an ice cooled solution of 1-(4-methoxy-phenyl)-5-(4-methylsulfonyl-phenyl)-3-trifluoromethyl-1H-1,2,4-triazole (10 g, 25.19 mmol) in THF (100 ml) was added dropwise a 2 M solution of n-butylmagnesium chloride in THF (21 ml, 42 mmol). Then the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was cooled to 0° C., a 1 M solution of triethylborane in THF (70 ml, 70 mmol) was added dropwise and the reaction mixture was refluxed for 18 h. After cooling, a solution of hydroxylamine-O-sulfonic acid (12 g, 106 mmol) and sodium acetate (17.38 g, 210 mmol) in H2O (140 ml) was added dropwise while maintaining the temperature below 15° C. Then the reaction mixture was stirred at room temperature for 2 h, the residue was extracted with ethyl acetate (2×100 ml), the organic layer was washed with saturated brine, dried over sodium sulfate and evaporated under vacuum. The resulting residue was chromatographed on silica gel using a 99/1 then 98/2 mixture of methylene chloride/methanol as the eluent, then recrystallized from ethanol to give a beige solid (2.5 g, 25%).

1. temperatureThe reaction mixture was cooled to 0° C.
2. temperaturethe reaction mixture was refluxed for 18 h
3. temperatureAfter cooling
4. temperaturewhile maintaining the temperature below 15° C
5. stirringThen the reaction mixture was stirred at room temperature for 2 h
6. extractionthe residue was extracted with ethyl acetate (2×100 ml)
7. washthe organic layer was washed with saturated brine
8. dry with materialdried over sodium sulfate
9. customevaporated under vacuum
10. customThe resulting residue was chromatographed on silica gel using a 99/1
11. addition98/2 mixture of methylene chloride/methanol as the eluent
12. customrecrystallized from ethanol

ORD record

ord-fdbef925e60d4a03be14bc93918bf84d

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06803380B1