6-BROMO-5-METHYL (1H)INDAZOLE

To a solution of 5-bromo-2, 4-dimethylaniline (15.09, 75.0 mmol) in chloroform (150 mL)was added Ac20 (15.0, 150 mmol) under ice bath. KOAc (8.009, 82.5 mmol), 18-crown-6 (10.0 g, 37.5 mmol) and isoamyl nitrite (26.3 g, 225 mmol) were added. The mixture was refluxed for36 hrs. The reaction mixture was concentrated and the residue was dissolved in EtOAc (500 mL). The organic solution was washed with water (100 mL), dried over Na2SO4 and concentrated. The residue was dissolved in THF (100 mL) and NaOH (4 M, 40.0 mL, 160 mmol) was added. The mixture was stirred at rt for I h. The solvent was removed under vacuum and the residue was partitioned between EtOAc (400 mL) and water (200 mL). Theorganic layer was washed with brine, dried over Na2SO4 and concentrated. The crude waspurified by column chromatography (PE: EtOAc from 10: 1 to 5: 1) to give the title compound(5.1 g, yield 32percent) as an orange solid.1H NMR (300 MHz, CDCI3): ö 10.20 (brs, 1H), 7.99 (s, 1H), 7.75 (s, 1H), 7.61 (s, IH), 2.50(s, 3H).To a solution of 5-bromo-2, 4-dimethylaniline (15.0 g, 75.0 mmol) in chloroform (150 mL) were added AcTo a solution of 5-bromo-2, 4-dimethylaniline (15.0 g, 75.0 mmol) in chloroform (150 mL) was added AcTo a solution of 5-bromo-2, 4-dimethylaniline (15.0 g, 75.0 mmcl) in chloroform (150 mL)was added Ac20 (15.0, 150 mmol) under ice bath. KOAc (8.00 g, 82.5 mmol), 18-crown-6(10.0 g, 37.5 mmol) and isoamyl nitrite (26.3 g, 225 mmol) were added. The mixture wasrefluxed for 36 hrs. The reaction mixture was concentrated and the residue was dissolved inEtOAc (500 mL). The organic solution was washed with water (100 mL), dried over Na2SO4and concentrated. The residue was dissolved in THE (100 mL) and NaOH (4 M, 40.0 mL, 160 mmol) was added. The mixture was stirred at rt for 1 h. The solvent was removedunder vacuum and the residue was partitioned between EtOAc (400 mL) and water (200 mL).The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crudewas purified by column chromatography (PE: EtOAc from 10: 1 to 5: 1) to give the titlecompound (5.1 g, yield 32percent) as an orange solid.1H NMR (300 MHz, CDCI3): 6 10.20 (br, 1H), 7.99 (s, 1H), 7.75 (s, 1H), 7.61 (s, 1H), 2.50 (s,

Molecular Weight:211.06
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes