7-Bromo-1H-indazole

A solution of 7-aminoindazole (3.45 g, 25.9 mmol) in concentrated HBr (25 mL) was diluted with water (8.5 mL) and cooled to -10° C. A cooled solution of sodium nitrite (755 mg, 10.9 mmol) in water (11.5 mL) was added slowly. More sodium nitrite (1.14 g, 16.5 mmol) was added portion-wise as a solid. The reaction solution was stirred at -5° C. for 15 min and then a cooled solution of CuBr (3.94 g, 27.5 mmol) in concentrated HBr (11.5 mL) was added drop-wise over a period of 15 min. The reaction mixture was stirred for 2 h at room temperature and was then neutralized with sat. NaHCO(ii) 7-Bromoindazole. (Coller, Aust. J. Chem. 27:2343 (1974)) A solution of 7-aminoindazole (3.45 g, 25.9 mmol) in concentrated HBr (25 mL) was diluted with water (8.5 mL) and cooled to -10° C. A cooled solution of sodium nitrite (755 mg, 10.9 mmol) in water (11.5 mL) was added slowly. More sodium nitrite (1.14 g, 16.5 mmol) was added portion-wise as a solid. The reaction solution was stirred at -5° C. for 15 min and then a cooled solution of CuBr (3.94 g, 27.5 mmol) in concentrated HBr (11.5 mL) was added drop-wise over a period of 15 min. The reaction mixture was stirred for 2 h at room temperature and was then neutralized with sat. NaHCO0225] (ii) 7-Bromoindazole. (Coller, Aust, J. Chem. 27:2343 (1974)) A solution of 7-aminoindazole (3.45 g, 25.9 mmol) in concentrated HBr (25 mL) was diluted with water (8.5 mL) and cooled to -1Ob) Preparation of intermediate 25A solution of intermediate 24 (1.7 g, 4.44 mmol) in DMSO (20 ml) was dropwise added to a solution of KOtBu (6.64 g, 59 mmol) in DMSO (50 ml). The r.m. was stirred for 2 hours at r.t. and was then poured on ice (300 g) containing a 1 N aqueous HCl solution (300 ml). The mixture was extracted with diethyl ether. The organic layer was separated, dried (MgSOIn water (41 ml) suspension of 2-bromo-6-methylaniline (4.17 g) was added concentrated hydrochloric acid (11.3mol/L, 5.95 mL). The reaction suspension, after dropping an aqueous solution of sodium nitrite (3.09 g, water 18 mL) at -3 °C , this mixture was stirred for 30 minutes at -3 °C. Under ice-cooling, after addition tetrafluoroborate sodium periodate solution (7.38 g, water 18 mL) stirred at room temperature for 3 hours. The precipitated solid was collected by filtration, to give compound Q4 (4.55 g) by drying. To chloroform suspension (45 mL) of potassium acetate compound Q4 (4.55 g) (3.91 g), and 18-crown-6 (0.42 g) was added, and this mixture was stirred at room temperature for 1 day. After completion of the reaction, ethyl acetate - it was separated by extraction with water, and the organic layer is dried over sodium sulfate, and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent; hexane: ethyl acetate = 3:1) was obtained compound Q5 (2.61 g) by purifying.

Molecular Weight:197.03
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes