5-BROMO-7-METHYL-1H-INDAZOLE

To a solution of 4-bromo-2, 6- dimethylaniline (51-51, 10 g, 0.05 mol) and potassium acetate (5.88 g, 0.06 mol) in CHC13 (120 mL) was added acetic anhydride (15.3 g, 0.15 mol) dropwise at 0 °C under an atmosphere ofnitrogen and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was heated to 60 °C and tert-butyl nitrite (10.3 g, 0.1 mol) was added dropwise. The resulting mixture was stirred overnight at 60 °C. The mixture was cooled to room temperature, diluted with H20, and extracted with DCM twice. The combined organic layers were washed by brine, dried over anhydrous Na2SO4, and concentrated to dryness. The remaining residue was dissolved inMeOH and 6 N aqueous HC1 (50 mL, v/v= 1:1) and the resulting mixture was stirred at room temperature for 4 hour. The reaction mixture was basified with 10 N aqueous NaOH and extracted with DCM. The organic layer was washed by brine, dried over anhydrous Na2SO4, and concentrated to afford 51-S2 (10.1 g, 95.7percent yield) as light a yellow solid. LC/MS (ESI) m/z: 212 (M+H) .-Bromo-7-methylindazole; Into a flame-dried round bottom flask, 4-bromo-2, 6-dimethylphenyldiazo- t-butyl sulfide (12.50 g, 41.5 mmol) and potassium t-butoxide (46.56 g, 10 equiv) were combined. A stir bar was added and the mixture placed under nitrogen. To this was added dry dimethylsulfoxide (120 mL). The mixture was stirred vigorously overnight at to room temperature. The reaction mixture was then carefully poured into a mixture of crushed ice (400 mL) and 10percent hydrochloric acid (200 mL). The resulting suspension was left to stand at 4°C overnight and the solid was collected by filtration and washed with water. The crude solid was dissolved in 5: 1 methylene chloride/methanol and the solution dried over magnesium sulfate and evaporated to give the product as an off-white solid (7.60 g, 87percent). 1H-NMR (CDCl3/CD30D, 500 MHz) 8 2.51 (3H, s), 7.22 (1H, s), 7.69 (1H, s), 7.94 (1H, s). Mass spec.: 211.03 (MH) +.Into a flame-dried round bottom flask, 4-bromo-2, 6-dimethylphenyldiazo-t- butyl sulfide (12.50 g, 41.5 mmol) and potassium t-butoxide (46.56 g, 10 equiv) were combined. A stir bar was added and the mixture placed under nitrogen. To this was added dry DMSO (120 mL). The mixture was stirred vigorously overnight at rt. The reaction mixture was then carefully poured into a mixture of crushed ice (400 mL) and [10percent] hydrochloric acid (200 mL). The resulting suspension was left to stand at [4°C] overnight and the solid was collected by filtration and washed with water. The crude solid was dissolved in 5: 1 methylene chloride/methanol and the solution dried over magnesium sulfate and evaporated to give the product as an off-white solid (7.60 g, [87percent). 1H-NMR (CDCL3/CD30D, ] 500 MHz) 8 2.51 (3H, s), 7.22 [(1H, ] s), 7.69 [(1H, ] s), 7.94 [(1H, ] s). Mass spec.: 211.03 [(MH) +.]Into a flame-dried round bottom flask, 4-bromo-2, 6-dimethylphenyldiazo-t-butyl sulfide (12.50 g, 41.5 mmol) and potassium t-butoxide (46.56 g, 10 equiv) were combined. A stir bar was added and the mixture placed under nitrogen. To this was added dry DMSO (120 mL). The mixture was stirred vigorously overnight at rt. The reaction mixture was then carefully poured into a mixture of crushed ice (400 mL) and 10percent hydrochloric acid (200 mL). The resulting suspension was left to stand at 4° C. overnight and the solid was collected by filtration and washed with water. The crude solid was dissolved in 5:1 methylene chloride/methanol and the solution dried over magnesium sulfate and evaporated to give the product as an off-white solid (7.60 g, 87percent).

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