[ CAS No. 633327-51-2 ] {[proInfo.proName]}

Name: 633327-51-2|6-Fluoro-5-nitro-1H-indazole|98%
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SKU: A185104
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Quality Control of [ 633327-51-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 633327-51-2 ]

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

Safety of [ 633327-51-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 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 ]
Downstream synthetic route of [ 633327-51-2 ]

[ 633327-51-2 ] Synthesis Path-Upstream 1~8

1
[ 633327-51-2 ]
[ 709046-14-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137

2
[ 348-25-4 ]
[ 633327-51-2 ]

Yield	Reaction Conditions	Operation 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

3
[ 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.

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

4
[ 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,

5
[ 709046-13-9 ]
[ 633327-51-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137

6
[ 446-10-6 ]
[ 633327-51-2 ]

Reference： [1] Patent: WO2015/104662, 2015, A1,
[2] Patent: US2016/326151, 2016, A1,

7
[ 366-49-4 ]
[ 633327-51-2 ]

Reference： [1] Patent: WO2016/4105, 2016, A1,

8
[ 633327-49-8 ]
[ 633327-51-2 ]

Reference： [1] Patent: WO2016/4105, 2016, A1,

[ 633327-51-2 ] Synthesis Path-Downstream 1~48

1
[ 348-25-4 ]
[ 633327-51-2 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sulfuric acid; potassium nitrate; at 0 - 20℃; for 0.166667h;	To a stined mixture of <strong>[348-25-4]6-fluoro-1H-indazole</strong> (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 0C, 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 %) as a yellow solid.?H NMR (400 MHz, DMSO-d6): oe 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%	With sulfuric acid; potassium nitrate; at 0 - 20℃; for 0.166667h;	To a stirred mixture of <strong>[348-25-4]6-fluoro-1H-indazole</strong> (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, 30%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 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)+.
30.3%	With sodium nitrate; sulfuric acid; at 0℃; for 2.5h;Large scale;	NaNO3 (5100mg, 60mmol) was placed in a 500mL reaction flask.60 mL of concentrated sulfuric acid, <strong>[348-25-4]6-fluoroindazole</strong> 1 (8167 mg, 60 mmol) were added dropwise thereto at 0 C.It was dissolved in 60 mL of concentrated sulfuric acid and the resulting solution was slowly added dropwise to a concentrated sulfuric acid solution of NaNO3, and the reaction was carried out at 0 C for 2.5 hours.The reaction solution was poured into 500 mL of ice-water mixture, and filtered with suction paper.The filtrate was extracted with EA, the organic phase and the solid phase obtained by suction filtration were combined and washed with saturated NaHCO3 and saturated NaCl in this order, dried over Na2SO4 and concentrated.Column chromatography (DCM) gave 2:3300 mg (30.3%) of a light yellow solid.

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]Patent: CN110642874,2020,A .Location in patent: Paragraph 0489-0491; 0499-0501
[4]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137

2
[ 633327-51-2 ]
[ 709046-14-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137

3
[ 367-29-3 ]
[ 633327-51-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,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,p. 2115 - 2137

5
[ 633327-51-2 ]
(1-benzyl-piperidin-4-yl)-(6-fluoro-1<i>H</i>-indazol-5-yl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137

6
[ 633327-50-1 ]
[ 633327-51-2 ]

Yield	Reaction Conditions	Operation in experiment
21%	With acetic acid; sodium nitrite; In water; for 2h;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, 21%). 1H NMR (300 MHz, DMSO): delta 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.
	With acetic acid; sodium sulfite; In water; at 20℃;	To a suspension of 2 g of 5-fluoro-2-methyl-4-nitro-phenylamine in 50 mL of glacial acetic acid, an aqueous solution of 812 mg of sodium sulfite was added, and stirred at room temperature overnight. The reaction solution was added with 100 mL of water, the precipitated powder filtered out, and the filtrate was concentrated to 50 mL. After extracting with 100 mL of ethyl acetate, the organic layer was washed successively with aqueous sodium hydrogen carbonate, 10% sodium thiosulfate aqueous solution, water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained crude crystals were triturated with toluene, to afford 589 mg of the title compound as bright yellow crystals.1H-NMR (400 MHz, DMSO-D6) delta 7.69 (1H, d, J = 11.6 Hz), 8.39 (1H, s), 8.79 (1H, d, J = 7.2 Hz), 13.76 (1H, s).

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

7
[ 633327-51-2 ]
[ 864082-72-4 ]

Yield	Reaction Conditions	Operation in experiment
84.3%	With sodium hypochlorite solution; In ethanol; at 20℃;Large scale;	Compound 2 (2000mg, 11mmol) was placed in a 250mL reaction flask.Add 50 mL of EtOH and NaOCl (20 mL, 55 mmol),The reaction was carried out at room temperature overnight. The reaction was monitored by TLC, acidified with 1N HCl, extracted with EA, washed with deionized water,Wash with saturated NaCl, dry with Na2SO4, remove the solvent under reduced pressure,Column chromatography (EA: PE = 1: 4) gave 8:2000 mg (84.3%) as a light yellow solid.
58%	With sodium hypochlorite; In ethanol; at 20℃; for 3h;	Example 39;. N-(3-Chloro-6-fluoro-lH indazol-5-yl)-4- (4-chloro-2-fluorophenyl)- 2-methyl-6-oxo-1, 4,5, 6-tetrahydro-3-pyridinecarboxamide;. Step 1;. 3-Chloro-6-fluoro-5-nitro-lH indazole;. 6-Fluoro-5-nitroindazole (850 mg, 4.693 mmol, 1.0 equiv) was dissolved in 20 mL EtOH, NaOCI (10 mL, 164.26 mmol, 35 equiv) was added and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated en vacuo to remove EtOH was then diluted with EtOAc and water. The phases were separated, and the organic phase was washed once with satd. NaHC03, and once with satd. NaCl. The organic phase was dried over Na2S04, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (10-100% EtOAc in Hexanes) to provide 583 mg (58%) of the title compound as a light orange solid. MS (ES+) m/e 216 [M+H] +
	With sodium hypochlorite; In ethanol; at 20℃; for 3h;	6-Fluoro-5-nitroindazole (850 mg, 4.693 mmol, 1.0 equiv) was dissolved in 20 mL EtOH, NaOCI (10 ml_, 164.26 mmol, 35 equiv) was added and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated en vacuo to remove EtOH was then diluted with EtOAc and water. The phases were separated, and the organic phase was washed once with satd. NaHC03, and once with satd. NaCI. The organic phase was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (10-100% EtOAc in Hexanes) to provide 583 mg (58%) of the title compound as a light orange solid. MS (ES+)m/e216[M+H]+.

Reference： [1]Patent: CN110642874,2020,A .Location in patent: Paragraph 0510-0513
[2]Patent: WO2005/82890,2005,A1 .Location in patent: Page/Page column 52
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 6631 - 6634
[4]Patent: WO2006/9889,2006,A1 .Location in patent: Page/Page column 57

8
[ 74-88-4 ]
[ 633327-51-2 ]
[ 1257303-08-4 ]
[ 1257303-13-1 ]

Yield	Reaction Conditions	Operation in experiment
42%		EXAMPLE 27 AA 100 niL flask was charged with sodium hydride (60% mineral oil dispersion, 0.100 g, 2.500 mmol) and tetrahydrofuran (20 mL). A solution of 6-fluoro-5-nitro-lH- indazole (0.362 g, 2.000 mmol) in tetrahydrofuran (10 mL) was added dropwise and the mixture was stirred for 30 minutes under nitrogen. The reaction mixture was cooled in an ice bath and a solution of iodomethane (0.498 ml, 8.00 mmol) in tetrathydrofuran (5 ml) was added dropwise. After stirring for 30 min, the ice bath was removed. The reaction was stirred for about 3 hours at ambient temperature, diluted with brine (80 ml), and extracted with ether (3 X 60 ml). The combined organics were dried over sodium sulfate, filtered, and concentrated to a brown solid which was purified by medium pressure liquid chromatography on silica gel eluted with a 10, 20, 40% ethyl acetate in hexanes step gradient to give the title compound 166 mg, 42%. MS (DCI(+)) m/e 196 (M+H)+, 213 (M+NH4)+. EXAMPLE 29 AThe title compound was obtained as one of the isomeric products in EXAMPLE 27A. MS: DCI m/e 196.2 (M+H)+.

Reference： [1]Patent: WO2010/138578,2010,A1 .Location in patent: Page/Page column 69; 71

9
[ 75-33-2 ]
[ 633327-51-2 ]
[ 1257303-01-7 ]

Yield	Reaction Conditions	Operation in experiment
54%	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 60℃;	EXAMPLE 23 AA mixture of 6-fluoro-5-nitro-lH-indazole (543 mg, 3 mmol), propane-2-thiol (308 muL, 3.30 mmol) and cesium carbonate (977 mg, 3.00 mmol) in anhydrous 1-methyl- 2-pyrrolidinone (5 mL) was stirred at 60 0C overnight and the quenched with water (30 mL). The mixture was extracted with dichloromethane. The organic solution was concentrated and the residue purified on a silica gel column, eluting with 60% ethyl acetate, to give the title compound as a yellow solid. 0.39 g, 54% yield. MS: (DCIZNH3) m/e 238.0 (M+H)+, 255.1 (M+NH4)+.

Reference： [1]Patent: WO2010/138578,2010,A1 .Location in patent: Page/Page column 65

10
[ 633327-51-2 ]
2-(2,6-dimethylpyridin-4-yl)-N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)oxazole-4-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

11
[ 633327-51-2 ]
2-methyl-5-nitro-6-(piperidin-1-yl)-2H-indazole [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

12
[ 633327-51-2 ]
1-methyl-5-nitro-6-(piperidin-1-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

13
[ 633327-51-2 ]
2-methyl-6-(piperidin-1-yl)-2H-indazol-5-amine [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

14
[ 633327-51-2 ]
N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)picolinamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

15
[ 633327-51-2 ]
N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)-6-(1H-pyrazol-4-yl)picolinamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

16
[ 633327-51-2 ]
1-methyl-6-(piperidin-1-yl)-1H-indazol-5-amine [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

17
[ 633327-51-2 ]
2-cyclopentyl-5-nitro-6-(piperidin-1-yl)-2H-indazole [ No CAS ]
1-cyclopentyl-5-nitro-6-(piperidin-1-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

18
[ 633327-51-2 ]
2-cyclopentyl-6-(piperidin-1-yl)-2H-indazol-5-amine [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

19
[ 633327-51-2 ]
N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)-2-(2-methylpyridin-4-yl)oxazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

20
[ 633327-51-2 ]
4-(2-cyclopentyl-5-nitro-2H-indazol-6-yl)morpholine [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

21
[ 633327-51-2 ]
2-cyclopentyl-6-morpholino-2H-indazol-5-amine [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

22
[ 633327-51-2 ]
N-(1-methyl-6-(piperidin-1-yl)-1H-indazol-5-yl)-2-(2-methylpyridin-4-yl)oxazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

23
[ 633327-51-2 ]
N-(2-cyclopentyl-6-(piperidin-1-yl)-2H-indazol-5-yl)-2-(2-methylpyridin-4-yl) oxazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

24
[ 633327-51-2 ]
1-cyclopropyl-5-nitro-6-(piperidin-1-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

25
[ 633327-51-2 ]
N-(2-cyclopentyl-6-morpholino-2H-indazol-5-yl)-2-(2-methylpyridin-4-yl)oxazole-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

26
[ 633327-51-2 ]
6'-amino-N-(2-cyclopentyl-6-morpholino-2H-indazol-5-yl)-[2,3'-bipyridine]-6-carboxamide 2,2,2-trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

27
[ 633327-51-2 ]
C₃₂H₃₇N₇O₄ [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1

28
[ 633327-51-2 ]
(S)-6-(1-(2-hydroxypropyl)-1H-pyrazol-4-yl)-N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)picolinamide [ No CAS ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

29
[ 110-89-4 ]
[ 633327-51-2 ]
5-nitro-6-(piperidin-1-yl)-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	at 80℃; for 14h;Sealed tube;	A solution of <strong>[633327-51-2]6-fluoro-5-nitro-1H-indazole</strong> (0.4 g, 2.20 mmol) and piperidine (2 mL) in a sealed tube was stifled at 80C for 14 h. After completion of reaction, reaction mixture was concentrated under reduced pressure. The crude compound was purified by column chromatography, eluting with a gradient (CH2C12:MeOH; 98:2) to give the title compound (0.37g, 68 %).?H NMR (400 MHz, CDC13): oe 10.4 (bs, 1H), 8.22 (s, 1H), 8.09 (s, 1H), 7.05 (s, 1H), 3.98-3.01(m, 4H), 1.78-1.72 (m, 4H), 1.63-1.50 (m, 2H). MS (ES) mle: 247 (M+1).
68%	at 80℃; for 14h;Sealed tube;	Step-4: Synthesis of 5-nitro-6-(piperidin-1-yl)-1H-indazole A solution of <strong>[633327-51-2]6-fluoro-5-nitro-1H-indazole</strong> (0.4 g, 2.20 mmol) and piperidine (2 mL) in a sealed tube was stirred at 80 C. for 14 h. After completion of reaction, reaction mixture was concentrated under reduced pressure. The crude compound was purified by column chromatography, eluting with a gradient (CH2Cl2:MeOH; 98:2) to give the title compound (0.37 g, 68%). 1H NMR (400 MHz, CDCl3): delta 10.4 (bs, 1H), 8.22 (s, 1H), 8.09 (s, 1H), 7.05 (s, 1H), 3.98-3.01 (m, 4H), 1.78-1.72 (m, 4H), 1.63-1.50 (m, 2H). MS (ES) m/e: 247 (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 0210

30
[ 137-43-9 ]
[ 633327-51-2 ]
2-cyclopentyl-6-fluoro-5-nitro-2H-indazole [ No CAS ]
1-cyclopentyl-6-fluoro-5-nitro-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%; 21%		A suspension of sodium hydride (1 g, 44.16 mmol) in dry DMF (20 mL) was cooled at 0C and 6-fluoro-5-nitro- 1H-indazole (4 g, 22.08 mmol) (product of step 3 in example 1) in dryDMF (20 mL) was added at the same temperature and stined for 30 mm. Cyclopentyl bromide(3.94 g, 26.49 mmol) was added drop wise to the above mixture and continued stifling at roomtemperature for 12 h. After completion of reaction, reaction mixture was poured on crushed iceand was extracted with ethyl acetate. The organic layer was washed with water followed by brine and dried over anhydrous Na2SO4. Organic layer was concentrated under reduced pressure to obtain crude compound, the crude residue was purified by flash chromatography (nhexane:EtOAc; 7:3) to give 1-cyclopentyl-<strong>[633327-51-2]6-fluoro-5-nitro-1H-indazole</strong> (Isomer B, 1.2 g, 21%)as a brown solid.?H NMR (400 MHz, DMSO-d6): oe 8.49 (d, J= 8Hz, 1H), 8.09 (s, 1H), 7.19 (d, J= 12Hz, 1H), 4.86-4.79 (m, 1H), 2. 14-2.11 (m, 4H), 2.09-1.87 (m, 2H), 1.75-1.60 (m, 2H). LCMS: mz: 250 (M-i-1, 100 %).Further elution of the column afforded the required product 2-cyclopentyl-6-fluoro-5-nitro-2H-indazole (Isomer A, 0.9 g, 16 %) as a brown solid.?H NMR (400 MHz, DMSO-d6): oe 8.85 (s, 1H), 8.78 (d, J = 8 Hz, 1H), 8.70 (d, J = 12 Hz, 1H),5.14-5.10 (m, 1H), 2.25-2.20 (m, 2H), 2.18-2.04 (m, 2H), 1.90-1.86 (m, 2H), 1.73-1.68 (m, 2H).LCMS: mlz: 250 (M+1) .
16%; 21%		A suspension of sodium hydride (1 g, 44.16 mmol) in dry DMF (20 mE) was cooled at 0 C. and 6-fluoro-5- nitro-1H-indazole (4 g, 22.08 mmol) (product of step 3 in example 1) in dry DMF (20 mE) was added at the same temperature and stirred for 30 mm Cyclopentyl bromide (3.94 g, 26.49 mmol) was added drop wise to the above mixture and continued stirring at room temperature for 12 h. After completion of reaction, reaction mixture was poured on crushed ice and was extracted with ethyl acetate. The organic layer was washed with water followed by brine and dried over anhydrous Na2504. Organic layer was concentrated under reduced pressure to obtain crude compound, the crude residue was purified by flash chromatography (n-hexane:EtOAc; 7:3) to give 1 -cyclopentyl-6-fluoro-5- nitro-1H-indazole (IsomerS, 1.2 g, 21%) as a brown solid. 10264] ?H NMR (400 MHz, DMSO-d5): oe 8.49 (d, J=8 Hz, 1H), 8.09 (s, 1H), 7.19 (d, J=12 Hz, 1H), 4.86-4.79 (m, 1H),2.14-2.11 (m, 4H), 2.09-1.87 (m, 2H), 1.75-1.60 (m, 2H). ECMS: mlz: 250 (MTh-i, 100%).Further elution of the column afforded the required product 2-cyclopentyl-6-fluoro-5-nitro-2H-indazole (Isomer A, 0.9 g, 16%) as a brown solid.?H NMR (400 MHz, DMSO-d5): oe 8.85 (s, 1H),8.78 (d, J=8 Hz, 1H), 8.70 (d, J=12 Hz, 1H), 5.14-5.10 (m, 1H), 2.25-2.20 (m, 2H), 2.18-2.04 (m, 2H), 1.90-1.86 (m, 2H), 1.73-1.68 (m, 2H). ECMS: mlz: 250 (M+1)

Reference： [1]Patent: WO2015/104662,2015,A1 .Location in patent: Page/Page column 49; 50
[2]Patent: US2016/326151,2016,A1 .Location in patent: Paragraph 0263; 0264; 0265

31
[ 446-10-6 ]
[ 633327-51-2 ]

Reference： [1]Patent: WO2015/104662,2015,A1
[2]Patent: US2016/326151,2016,A1

32
[ 420-37-1 ]
[ 633327-51-2 ]
[ 1257303-13-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethyl acetate; at 20℃; for 5h;	Preparation 47E: 6-Fluoro-2-methyl-5-nitroindazole To a solution of 6-fluoro-5-nitro-lH-indazole (1.14 g, 6.30 mmol) in EA (150 mL) was added BF4-OMe3 (1.397 g, 9.45 mmol) at rt. The mixture was stirred for 5 hr at r.t. aq NaHC03 was added to adjust pH = 7-8, extracted with EA, dried, concentrated to afford the title compound (1 g, 81%). [M+H] Calc'd for C8H6FN302, 196; Found, 196.

Reference： [1]Patent: WO2016/4105,2016,A1 .Location in patent: Paragraph 00146

33
[ 366-49-4 ]
[ 633327-51-2 ]

Reference： [1]Patent: WO2016/4105,2016,A1

34
[ 633327-49-8 ]
[ 633327-51-2 ]

Reference： [1]Patent: WO2016/4105,2016,A1

35
[ 633327-51-2 ]
6-fluoro-2-methylindazol-5-amine [ No CAS ]

Reference： [1]Patent: WO2016/4105,2016,A1

36
[ 633327-51-2 ]
4-bromo-3-fluoro-N-(6-fluoro-2-methylindazol-5-yl)benzenecarboximidamide [ No CAS ]

Reference： [1]Patent: WO2016/4105,2016,A1

37
[ 633327-51-2 ]
1-cyclopentyl-5-nitro-6-(piperidin-1-yl)-1H-indazole [ No CAS ]
2-cyclopentyl-5-nitro-6-(piperidin-1-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: US2016/326151,2016,A1

38
[ 633327-51-2 ]
N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)-6-(1H-pyrazol-4-yl)picolinamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/326151,2016,A1

39
[ 633327-51-2 ]
2-(2-aminopyridin-4-yl)-N-(2-methyl-6-(piperidin-1-yl)-2H-indazol-5-yl)oxazole-4-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/326151,2016,A1

40
[ 633327-51-2 ]
C₂₀H₂₆N₄O₈S [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

41
[ 633327-51-2 ]
C₂₀H₂₆N₄O₅S [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

42
[ 633327-51-2 ]
C₂₁H₂₈N₄O₅S [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

43
[ 633327-51-2 ]
C₂₁H₃₂N₄O₈Si [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

44
[ 633327-51-2 ]
C₂₁H₃₂N₄O₅Si [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

45
[ 633327-51-2 ]
C₂₂H₃₄N₄O₅Si [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

46
[ 633327-51-2 ]
C₂₁H₁₉N₇O₃ [ No CAS ]

Reference： [1]Patent: CN110642874,2020,A

47
[ 24424-99-5 ]
[ 633327-51-2 ]
C₁₂H₁₂FN₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; at 20℃; for 2h;Large scale;	Compound 2 (1449mg, 8mmol) was placed in a 250mL reaction flask, and Boc2O (2095mg, 9.6mmol), DMAP (195mg, 1.6mmol),100mL THF, reacted at room temperature for 2h, TLC monitored the end of the reaction, EA extraction,Wash with deionized water, wash with saturated NaCl, dry with Na2SO4,The solvent was removed under reduced pressure to give a Boc protected intermediate. This intermediate was isolated without further purification,Used directly in the next step. N-Boc-L-cysteine (2655mg, 12mmol), Cs2CO3 (7819mg, 24mmol) were placed in a 250mL reaction flask,80 mL of DMF was added thereto at 0 C. and reacted for 15 min, and then a solution of the Boc-protected intermediate DMF (20 mL) obtained in reaction a was slowly added dropwise, and the reaction was performed at 0 C. overnight.The reaction was monitored by TLC, acidified with 0.2M HCl, extracted with EA, washed with deionized water,Wash with saturated NaCl, dry with Na2SO4, remove the solvent under reduced pressure,Column chromatography (DCM: MeOH = 20: 1) gave 3:Light yellow solid 2400mg(62.2%).

Reference： [1]Patent: CN110642874,2020,A .Location in patent: Paragraph 0489-0490; 0492

48
[ 76513-69-4 ]
[ 633327-51-2 ]
C₁₃H₁₈FN₃O₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.2%		Compound 2 (1086.8mg, 6mmol) was placed in a 250mL reaction flask.Cs2CO3 (2443 mg, 7.5 mmol) was added thereto, 40 mL of DMF was added thereto at 0 C and reacted for 15 min, and then SEMCl (1.33 mL, 7.5 mmol) was slowly added dropwise,After the dropwise addition, it was transferred to room temperature and reacted for 4h. The reaction was monitored by TLC and the EA extraction was performed.Wash with deionized water, wash with saturated NaCl, dry with Na2SO4,The solvent was removed under reduced pressure, and column chromatography (EA: PE = 1: 8) gave 5:900 mg (48.2%) of a light yellow solid.

Reference： [1]Patent: CN110642874,2020,A .Location in patent: Paragraph 0499-0500; 0502

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H200	Unstable explosive
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Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
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H303	May be harmful if swallowed
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H311	Toxic in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
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H320	Causes eye irritation
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Code	Phrase
H400	Very toxic to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 633327-51-2 ] {[proInfo.proName]}

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[ 633327-51-2 ] Synthesis Path-Upstream 1~8

[ 633327-51-2 ] Synthesis Path-Downstream 1~48

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Fluorinated Building Blocks

Nitroes

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