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Chemical Structure| 633327-51-2 Chemical Structure| 633327-51-2
Chemical Structure| 633327-51-2

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6-Fluoro-5-nitro-1H-indazole

CAS No.: 633327-51-2

4.5 *For research use only!

Cat. No.: A185104 Purity: 98%

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Product Details of [ 633327-51-2 ]

CAS No. :633327-51-2
Formula : C7H4FN3O2
M.W : 181.12
MDL No. :MFCD09261136
Boiling Point : No data available
InChI Key :CQWPKRSNPVUHQA-UHFFFAOYSA-N
Pubchem ID :45933667

Safety of [ 633327-51-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis [ 633327-51-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 633327-51-2 ]

[ 633327-51-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 348-25-4 ]
  • [ 633327-51-2 ]
YieldReaction ConditionsOperation in experiment
30% at 0 - 20℃; for 0.166667 h; To a stined mixture of 6-fluoro-1H-indazole (1 g, 0.OO7mol) and Conc. H2S04 (22 mL),KNO3 (0.74 g, 0.OO7mol) was added portion wise at 0 °C, and stifling was continued at RT for10 mm. After completion of reaction, reaction mixture was cooled to 0°C, basified with saturatedNaHCO3 solution, extracted with EtOAc, washed with brine and the organic layer was dried overanhydrous Na2SO4. After concentration under reduced pressure, the crude residue was purifiedby flash chromatography (DCMIMeOH 9.8:0.2) to give the title compound (0.4 g, 30 percent) as a yellow solid.‘H NMR (400 MHz, DMSO-d6): ö 13.7 (bs, 1H), 8.78 (d, J = 7.4 Hz, 1H), 8.34 (s, 1H), 7.68 (d,J= 11.8 Hz, 1H). MS (ES) mle: 180 (M-1).
30% at 0 - 20℃; for 0.166667 h; To a stirred mixture of 6-fluoro-1H-indazole (1 g, 0.007 mol) and Conc. H2SO4 (22 mL), KNO3 (0.74 g, 0.007 mol) was added portion wise at 0° C., and stirring was continued at RT for 10 min After completion of reaction, reaction mixture was cooled to 0° C., basified with saturated NaHCO3 solution, extracted with EtOAc, washed with brine and the organic layer was dried over anhydrous Na2SO4.
After concentration under reduced pressure, the crude residue was purified by flash chromatography (DCM/MeOH 9.8:0.2) to give the title compound (0.4 g, 30percent) as a yellow solid.
1H NMR (400 MHz, DMSO-d6): δ 13.7 (bs, 1H), 8.78 (d, J=7.4 Hz, 1H), 8.34 (s, 1H), 7.68 (d, J=11.8 Hz, 1H). MS (ES) m/e: 180 (M-1)+.
Reference: [1] Patent: WO2015/104662, 2015, A1, . Location in patent: Page/Page column 38
[2] Patent: US2016/326151, 2016, A1, . Location in patent: Paragraph 0208
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137
  • 2
  • [ 633327-50-1 ]
  • [ 633327-51-2 ]
YieldReaction ConditionsOperation in experiment
21% With acetic acid; sodium nitrite In water for 2 h; Cooling with ice Preparation 47D: 6-Fluoro-5-nitro-lH-indazole
To a solution of 5-fluoro-2-methyl-4-nitroaniline (4.9 g, 28.82 mmol) in AcOH (50 mL) was added NaNC>2 (2.18 g, 31.71 mmol) in water (5 mL) in ice-bath. The mixture was stirred for 2 hr in ice-bath. H20 was added and extracted with EA, dried, concentrated and purified by flash chromatography on silica gel (PE/EA=3/1) to afford the title compound (1.14 g, 21percent). 1H NMR (300 MHz, DMSO): δ 7.86 (1H, d, J=12.0 Hz), 8.36 (1H, s), 8.76 (1H, d, J= 7.2 Hz), 13.71 (1H, s). [M+H] Calc'd for C7H4FN302, 182; Found, 182.
Reference: [1] Patent: WO2016/4105, 2016, A1, . Location in patent: Paragraph 00146
[2] Patent: EP1510516, 2005, A1, . Location in patent: Page/Page column 101-102
  • 3
  • [ 367-29-3 ]
  • [ 633327-51-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137
[2] Patent: WO2015/104662, 2015, A1,
[3] Patent: WO2016/4105, 2016, A1,
[4] Patent: US2016/326151, 2016, A1,
  • 4
  • [ 709046-13-9 ]
  • [ 633327-51-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137
  • 5
  • [ 446-10-6 ]
  • [ 633327-51-2 ]
Reference: [1] Patent: WO2015/104662, 2015, A1,
[2] Patent: US2016/326151, 2016, A1,
  • 6
  • [ 366-49-4 ]
  • [ 633327-51-2 ]
Reference: [1] Patent: WO2016/4105, 2016, A1,
  • 7
  • [ 633327-49-8 ]
  • [ 633327-51-2 ]
Reference: [1] Patent: WO2016/4105, 2016, A1,
 

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