Potassium Carbonate → 6-bromo-3-ethyl-1-phenyl-1H-indazole

Into a 1000-mL 3-necked round-bottom flask, was placed a solution of (Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine and (E)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine (44.3 g, 138.01 mmol, 1.00 equiv) in N,N-dimethylformamide (400 mL), potassium carbonate (83 g, 601.45 mmol, 4.40 equiv). The resulting solution was stirred for 2 days at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with water (500 mL). The resulting solution was extracted with ethyl acetate (2×300 mL) and the organic layers combined. The resulting mixture was washed with water (2×300 mL) and brine (1×300 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:50) to yield 6-bromo-3-ethyl-1-phenyl-1H-indazole as a yellow solid.

1. customInto a 1000-mL 3-necked round-bottom flask, was placed
2. concentrationThe resulting mixture was concentrated under vacuum
3. additionThe resulting solution was diluted with water (500 mL)
4. extractionThe resulting solution was extracted with ethyl acetate (2×300 mL)
5. washThe resulting mixture was washed with water (2×300 mL) and brine (1×300 mL)
6. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-abdf7059708c4ed3933b2679f4cff480

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822447B2