5-AMINO-3-BROMO (1H)INDAZOLE

Tin (II) chloride dihydrate (100.4 g, 44.62 mmol) was added portionwise to a solution of 3-bromo-5-nitro-1H-indazole (18.0 g, 7.43 mmol) in ethanol (400 mL) at 0 °C. The reaction mixture was stirred for 14 h at 80 °C. The product was isolated and purified via standard methods to afford 3-bromo-1H-indazol-5-amine (14.5 g, 92percent) as light brown solid.Tin dichloride dihydrate (846 mg, 3.75 mmol) was added to a solution of 3-bromo-5-nitro-1H-indazole (181 mg, 0.748 mmol) in N, N-dimethylformamide (3 ml), and the resulting mixture was stirred at 70°C for 1.5 hours. After an aqueous sodium hydrogensulfite solution was added thereto to terminate the reaction, ethyl acetate was added to the reaction mixture and the insoluble material was removed by filtration using Celite. The residue was extracted with ethyl acetate/toluene, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 3-bromo-1H-indazol-5-amine (110 mg, 69percent) was obtained.1H-NMR (DMSO-d6) δ; 5.01 (2H, br), 6.53 (1H, d, J=1.7Hz), 6.84 (1H, dd, J=2.1, 8.9Hz), 12.90 (1H, br).

Molecular Weight:212.05
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:210.97451
Monoisotopic Mass:210.97451
Topological Polar Surface Area:54.7
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes