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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): ? 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 ]
Yield
Reaction Conditions
Operation 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.
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