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1.00 g (5.06 mmol) of 3-chloro-5-nitro-1H-indazole wassuspended in 50 ml of ethanol, and 5.71 g (25.3 mmol) of tin(II) chloridedihydrate were added. The mixture was left to stir at reflux overnight,saturated aqueous sodium bicarbonate solution was then added and the mixturewas extracted three times with ethyl acetate. The combined organic phases weredried over magnesium sulphate and the solvent was removed under reducedpressure. The mixture was triturated with ten'-butyl methyl ether and the solidwas filtered off with suction. Yield: 544 mg (purity 90percent, 58percent of theory)
Reference：
[1] Journal of Chemical Research, Miniprint, 1990, # 11, p. 2601 - 2615
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 26, p. 5663 - 5673
[3] Patent: US2016/52884, 2016, A1, . Location in patent: Paragraph 0649-0652
[4] Patent: KR2015/137095, 2015, A, . Location in patent: Paragraph 0867-0870
With tin(II) chloride dihdyrate; In ethanol; for 4h;Reflux;
To a solution of 3-chloro-5-nitro-lH-indazole (7) (310 mg, 1.57 mmol) in ethanol (150 mL) was added stannous chloride dihydrate (1.77 g, 7.85 mmol). The reaction mixture was refluxed for 4 h. After completion of reaction, the mixture was concentrated on rotary evaporator. The residue was diluted with dichloromethane and basified with sodium hydroxide. The mixture was transferred to separatory funnel and the aqueous layer was extracted with dichloromethane The combined organic layer was dried over anhydrous magnesium sulfate, fi tered, and concentrated in vacuo. The residue was purified by flash chromatography to provide 3-chloro-lH-indazol-5-amine (10) (186 mg, 71 yield), m/z 168 [M+H]+.
With tin(II) chloride dihdyrate; In ethanol;Reflux;
[0650] 1.00 g (5.06 mmol) of<strong>[4812-45-7]3-chloro-5-nitro-1H-indazole</strong>was suspended in 50ml of ethanol, and5.71 g (25.3 mmol) oftin(II) chloride dihydrate were added. The mixture was left tostir at reflux overnight, saturated aqueous sodium bicarbonatesolution was then added and the mixture was extracted threetimes with ethyl acetate. The combined organic phases weredried over magnesium sulphate and the solvent was removedunder reduced pressure. The mixture was triturated with tertbutylmethyl ether and the solid was filtered off with suction.Yield: 544 mg (purity 90%, 58% of theory)[0651] LC/MS [Method 5]: R,=l.50 min; MS (ESipos):m/z=168 (M+H)+,[0652] 1H-NMR (400 MHz, DMSO-d6): o [ppm]=12.8 (s,lH), 7.28 (d, lH), 6.89 (dd, lH), 6.66 (m, lH), 5.46 (br. s, 2H).
544 mg
With tin(II) chloride dihdyrate; In ethanol;Reflux;
1.00 g (5.06 mmol) of <strong>[4812-45-7]3-chloro-5-nitro-1H-indazole</strong> wassuspended in 50 ml of ethanol, and 5.71 g (25.3 mmol) of tin(II) chloridedihydrate were added. The mixture was left to stir at reflux overnight,saturated aqueous sodium bicarbonate solution was then added and the mixturewas extracted three times with ethyl acetate. The combined organic phases weredried over magnesium sulphate and the solvent was removed under reducedpressure. The mixture was triturated with ten'-butyl methyl ether and the solidwas filtered off with suction. Yield: 544 mg (purity 90%, 58% of theory)
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