Hydrochloric Acid → HCID 22933895, compound

Under nitrogen, 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-ol (200 mg, 0.861 mmol) was dissolved in N,N-dimethylformamide (5 ml), followed by adding thereto 4-fluoronitrobenzene (100 μl, 0.947 mmol) and potassium carbonate (179 mg, 1.29 mmol), and the resulting mixture was stirred at 50° C. for 1 hour. After the reaction solution was cooled to room temperature, a 1N-aqueous hydrochloric acid solution (6 ml) and methanol (3 ml) were added thereto and the resulting mixture was stirred at room temperature for 2 hours. The mixture was adjusted to pH 9 with a saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate/toluene=3/1. The combined extract layer was washed with water and then a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to obtain 4-methyl-5-(4-nitrophenoxy)-1H-indazole (192 mg, yield 82.8%) as a yellow solid.

1. additionby adding
2. extractionextracted twice with ethyl acetate/toluene=3/1
3. extractionThe combined extract layer
4. washwas washed with water
5. dry with materiala saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate
6. filtrationfiltered
7. distillationThe solvent was distilled off under reduced pressure
8. concentrationthe resulting concentration residue
9. customwas purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

ORD record

ord-4fefd20c19884956baec5d50d5f60c1d

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2