5-heteroaryl substituted indazoles as kinase inhibitors
A compound, heteroaryl technology, applied in the field of 5-heteroaryl substituted indazole compounds used as kinase inhibitors, can solve the problem of neurotoxic effect block and so on
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Embodiment 1
[0662] 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-1H-indazole and 5-(1-benzyl-1H-1,2,3-triazole-5- base)-1H-indazole mixture;
Embodiment 1A
[0664] tert-Butyl 5-iodo-1H-indazole-1-carboxylate
[0665] To an ice-bath-cooled solution of 4-iodo-2-methylaniline (20 g, 83.24 mmol) in chloroform (250 mL) was added dropwise a solution of acetic anhydride (21.2 g, 208.11 mmol) in chloroform (50 mL). After the addition was complete, the mixture was stirred at room temperature for 1 hour. Potassium acetate (2.5 g, 24.97 mmol) and isoamyl nitrite (22.3 mL, 166.48 mmol) were added, and the mixture was heated at 70° C. for 20 hours. The cooled mixture was washed with saturated NaHCO 3 The aqueous solution was quenched to pH 7. The mixture was extracted with dichloromethane, the organic layer was dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The crude solid was washed with methanol, dissolved in tetrahydrofuran (200 mL), and treated with hot KOH (60 g) in water (200 mL). The resulting mixture was stirred for 15 minutes and treated to pH 1 with 6N HCl. The layers were separated, ...
Embodiment 1B
[0667] tert-butyl 5-((trimethylsilyl)ethynyl)-1H-indazole-1-carboxylate
[0668] Example 1A (10.81 g, 31.4 mmol), dichlorobis(triphenylphosphine)palladium(II) (1.1 g, 1.57 mmol) and cuprous(I) iodide (365 mg, 1.92 mmol) were mixed under inert gas Mix in triethylamine (70 mL). Trimethylsilylacetylene (5.0 mL, 36.0 mmol) was added, and the resulting mixture was stirred at 60°C overnight. The solvent was distilled off under reduced pressure, and the resulting residue was dissolved in dichloromethane and washed with 1N hydrochloric acid. The resulting mixture was adsorbed on silica gel and purified by silica gel chromatography eluting with a gradient of 5-40% ethyl acetate in hexanes to afford the title compound. MS(ESI+)m / z 215.0(M-99) + .
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