[ CAS No. 54705-91-8 ] {[proInfo.proName]}

Name: 54705-91-8|2-(1-Pyrazolyl)aniline|98%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 54705-91-8 ]

CAS No. :	54705-91-8	MDL No. :	MFCD03086227
Formula :	C₉H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UIYKQBXRFZCXFX-UHFFFAOYSA-N
M.W :	159.19	Pubchem ID :	2779710
Synonyms :

Safety of [ 54705-91-8 ]

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

Application In Synthesis of [ 54705-91-8 ]

* 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.

Downstream synthetic route of [ 54705-91-8 ]

[ 54705-91-8 ] Synthesis Path-Downstream 1~53

1
[ 25688-17-9 ]
[ 54705-91-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen In ethanol for 3h; Ambient temperature;
95%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; Inert atmosphere;
95%	With palladium on activated carbon; hydrogen In ethanol

93%	With hydrazine hydrate In ethanol for 1h; Heating;
87%	With hydrazine hydrate In methanol for 4h; Heating;
74%	With hydrogen In ethanol
	With palladium on activated charcoal; hydrazine hydrate In ethanol for 8h; Reflux; Heating;	3.2.2. Synthesis of 2-(Benzo[d]thiazol-2-yl)anilines 2 and 8a-8m General procedure: In a 100 mL three-necked flask equipped with a dropping funnel, 2-(2-nitrophenyl)benzo[d]- thiazole (1, 3.0 g, 12.5 mmol) and ethanol (50 mL) were mixed and heated to reflux. Palladized charcoal (0.1 g, 5%) was added, then 80% hydrazine hydrate solution (10 mL) was added from a dropping funnel during 30 min [10,11]. The heating was continued for 8 h and then the mixture cooled. The solid was filtered off and the filtrate was concentrated to give a crude product that was recrystallized from ethyl acetate and petroleum ether solution (1:5) to afford compound 2 as a yellow powder (yield: 3.76 g, 85%).
	With iron; ammonium chloride In ethanol; water at 80℃;

Reference： [1]Albini, Angelo; Bettinetti, Gianfranco; Minoli, Giovanna [Journal of Organic Chemistry, 1984, vol. 49, # 15, p. 2670 - 2676]
[2]Lee, Wan-Chen Cindy; Shen, Yuning; Gutierrez, David A.; Li, Jie Jack [Organic Letters, 2016, vol. 18, # 11, p. 2660 - 2663]
[3]Shen, Yuning; Cindy Lee, Wan-Chen; Gutierrez, David A.; Li, Jie Jack [Journal of Organic Chemistry, 2017, vol. 82, # 21, p. 11620 - 11625]
[4]De La Hoz, Antonio; Díaz-Ortiz, Angel; Elguero, José; Martínez, Luis J.; Moreno, Andrés; Sánchez-Migallón, Ana [Tetrahedron, 2001, vol. 57, # 20, p. 4397 - 4403]
[5]Black, David St.C.; Deacon, Glen B.; Edwards, Gavin L. [Australian Journal of Chemistry, 1991, vol. 44, # 12, p. 1771 - 1781]
[6]Lindley, John M.; McRobbie, Ian M.; Meth-Cohn, Otto; Suschitzky, Hans [Journal of the Chemical Society. Perkin transactions I, 1980, p. 982 - 994]
[7]Du, Shijie; Tian, Zaimin; Yang, Dongyan; Li, Xiuyun; Li, Hong; Jia, Changqing; Che, Chuanliang; Wang, Mian; Qin, Zhaohai [Molecules, 2015, vol. 20, # 5, p. 8395 - 8408]
[8]Yan, Qi; Chen, Yuzhe; Tang, Baiyou; Xiao, Qiang; Qu, Rong; Tong, Linjiang; Liu, Jian; Ding, Jian; Chen, Yi; Ding, Ning; Tan, Wenfu; Xie, Hua; Li, Yingxia [European Journal of Medicinal Chemistry, 2018, vol. 152, p. 298 - 306]

2
[ 90460-16-5 ]
[ 54705-91-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride In acetone for 0.166667h; Heating;

Reference： [1]Albini, Angelo; Bettinetti, Gianfranco; Minoli, Giovanna [Journal of Organic Chemistry, 1984, vol. 49, # 15, p. 2670 - 2676]

3
[ 105-36-2 ]
[ 54705-91-8 ]
(2-Pyrazol-1-yl-phenylamino)-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 40h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

4
[ 17639-93-9 ]
[ 54705-91-8 ]
[ 78786-65-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 40h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

5
[ 7476-66-6 ]
[ 54705-91-8 ]
Phenyl-(2-pyrazol-1-yl-phenylamino)-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 40h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

6
[ 1738-57-4 ]
[ 134817-14-4 ]
[ 54705-91-8 ]
[ 1738-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	With di-n-propylamine In benzene for 4h; Irradiation; Yield given. Yields of byproduct given;

Reference： [1]Albini, A.; Bettinetti, G.; Minoli, G. [Journal of the American Chemical Society, 1991, vol. 113, # 18, p. 6928 - 6934]

7
[ 544-92-3 ]
[ 151-50-8 ]
[ 54705-91-8 ]
[ 25775-03-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 2-(1H-pyrazol-1-yl)aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: copper(I) cyanide; potassium cyanide In water at 60℃; for 0.333333h;

Reference： [1]De La Hoz, Antonio; Díaz-Ortiz, Angel; Elguero, José; Martínez, Luis J.; Moreno, Andrés; Sánchez-Migallón, Ana [Tetrahedron, 2001, vol. 57, # 20, p. 4397 - 4403]

8
[ 108-77-0 ]
[ 54705-91-8 ]
6-chloro-N,N'-bis-(2-pyrazol-1-yl-phenyl)-[1,3,5]triazine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 65℃; for 26h;
	With N-ethyl-N,N-diisopropylamine

Reference： [1]Diaz-Ortiz, Angel; Elguero, Jose; Foces-Foces, Concepcion; De la Hoz, Antonio; Moreno, Andres; Moreno, Sergio; Sanchez-Migallon, Ana; Valiente, Gema [Organic and Biomolecular Chemistry, 2003, vol. 1, # 24, p. 4451 - 4457]
[2]Location in patent: body text Moral, Mónica; Ruiz, Amparo; Moreno, Andrés; Díaz-Ortiz, Angel; López-Solera, Isabel; de la Hoz, Antonio; Sánchez-Migallón, Ana [Tetrahedron, 2010, vol. 66, # 1, p. 121 - 127]

9
[ 60418-63-5 ]
[ 109-89-7 ]
[ 54705-91-8 ]
[ 1738-59-6 ]
7H-2-diethylamino-7-pyrazolylazepine [ No CAS ]
3H-2-diethylamino-7-pyrazolylazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 19.85℃; UV-irradiation;

Reference： [1]Carra, Claudio; Bally, Thomas; Albini, Angelo [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5552 - 5562]

10
[ 288-13-1 ]
[ 615-36-1 ]
[ 54705-91-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine In toluene at 110℃; for 24h;
85%	With potassium phosphate; benzoin oxime; copper diacetate In dimethyl sulfoxide at 80℃; Inert atmosphere;	General Procedure for Catalytic Experiments General procedure: K3PO4 (5.62 mmol) in DMSO (4 mL), were added Cu(OAc)2 (0.28 mmol). The flask was evacuatedand backfilled with argon for three times. The resulting suspension was heated in a 80 °C oil bathwith stirring for the indicated time. The reactor was cooled to r.t., the flask was opened to air and thereaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 mL × 3), andorganic layer was washed with water (20 mL × 2) and once with brine (25 mL), dried overmagnesium sulfate and concentrated in vacuo. The product was purified by column chromatographyon silica gel using petroleum ether and ethyl acetate as eluent.1-(2-Methoxyphenyl)-1H-pyrrole (3a) [30]: colorless oil (0.43 g, 88%). 1H-NMR (400 MHz, CDCl3) δ (ppm):7.30-7.23 (2H, m), 7.03-6.98 (4H, m), 6.30 (2H,
82%	With quebrachitol; copper; caesium carbonate In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Green chemistry;

77%

With potassium carbonate; N,N`-dimethylethylenediamine In xylene for 36h; Heating;

Reference： [1]Antilla, Jon C.; Baskin, Jeremy M.; Barder, Timothy E.; Buchwald, Stephen L. [Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5578 - 5587]
[2]Yuan, Chunling; Zhang, Lei; Zhao, Yingdai [Molecules, 2019, vol. 24, # 22]
[3]Zhou, Qifan; Du, Fangyu; Chen, Yuanguang; Fu, Yang; Sun, Wenjiao; Wu, Ying; Chen, Guoliang [Journal of Organic Chemistry, 2019, vol. 84, # 12, p. 8160 - 8167]
[4]Liddle, Brendan J.; Silva, Rosalice M.; Morin, Tyler J.; Macedo, Felipe P.; Shukla, Ruchi; Lindeman, Sergey V.; Gardinier, James R. [Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5637 - 5646]

11
[ 960-71-4 ]
[ 54705-91-8 ]
C₆H₄NHN₂C₃H₃BC₁₂H₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In toluene Heating;

Reference： [1]Liddle, Brendan J.; Silva, Rosalice M.; Morin, Tyler J.; Macedo, Felipe P.; Shukla, Ruchi; Lindeman, Sergey V.; Gardinier, James R. [Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5637 - 5646]

12
[ 3034-19-3 ]
[ 54705-91-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 77 percent / H₂SO₄ / ethanol / 4 h / Heating 2: 93 percent / hydrazine hydrate / Pd/C / ethanol / 1 h / Heating
	Multi-step reaction with 2 steps 1: 81 percent / 98percent sulphuric acid / ethanol; acetic acid / 6 h / Heating 2: 74 percent / hydrogen / Raney nickel / ethanol

Reference： [1]De La Hoz, Antonio; Díaz-Ortiz, Angel; Elguero, José; Martínez, Luis J.; Moreno, Andrés; Sánchez-Migallón, Ana [Tetrahedron, 2001, vol. 57, # 20, p. 4397 - 4403]
[2]Lindley, John M.; McRobbie, Ian M.; Meth-Cohn, Otto; Suschitzky, Hans [Journal of the Chemical Society. Perkin transactions I, 1980, p. 982 - 994]

13
[ 60418-63-5 ]
[ 54705-91-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 77 mg / acetonitrile / 0.67 h / Irradiation 2: di-n-propylamine / benzene / 4 h / Irradiation

Reference： [1]Albini, A.; Bettinetti, G.; Minoli, G. [Journal of the American Chemical Society, 1991, vol. 113, # 18, p. 6928 - 6934]

14
[ 400743-82-0 ]
[ 20012-63-9 ]
[ 39643-31-7 ]
[ 728918-72-7 ]
C₈H₇F₄N [ No CAS ]
C₃₃H₂₉IN₅O₄Pol [ No CAS ]
[ 91646-45-6 ]
[ 4273-98-7 ]
[ 2264-92-8 ]
[ 1204-44-0 ]
[ 68817-71-0 ]
[ 369-36-8 ]
[ 37750-29-1 ]
[ 55751-54-7 ]
[ 18595-14-7 ]
[ 52562-19-3 ]
[ 62532-99-4 ]
[ 21627-58-7 ]
[ 73818-73-2 ]
[ 54705-91-8 ]
[ 26286-54-4 ]
[ 177171-13-0 ]
[ 99-55-8 ]
[ 23491-48-7 ]
[ 400750-84-7 ]
C₄₂H₃₇N₈O₄Pol [ No CAS ]
C₄₂H₃₇N₈O₄Pol [ No CAS ]
C₄₃H₄₃N₆O₄Pol [ No CAS ]
C₄₂H₃₉N₆O₄Pol [ No CAS ]
C₄₃H₃₇N₆O₄PolS [ No CAS ]
C₄₀H₃₆N₇O₆Pol [ No CAS ]
C₄₂H₃₉N₆O₆Pol [ No CAS ]
C₃₉H₃₃FN₇O₆Pol [ No CAS ]
C₄₄H₃₉N₆O₅Pol [ No CAS ]
C₄₅H₃₈ClN₆O₄Pol [ No CAS ]
C₄₆H₄₁N₆O₄Pol [ No CAS ]
C₄₃H₄₂N₇O₄Pol [ No CAS ]
C₄₆H₄₁N₆O₅Pol [ No CAS ]
C₄₅H₃₈FN₆O₄Pol [ No CAS ]
C₄₅H₃₈ClN₆O₄Pol [ No CAS ]
C₄₁H₃₅F₄N₆O₄Pol [ No CAS ]
C₄₅H₃₉N₆O₆PolS [ No CAS ]
C₄₅H₃₈ClN₆O₄PolS [ No CAS ]
C₄₄H₄₄N₇O₄Pol [ No CAS ]
C₄₇H₄₁N₆O₅Pol [ No CAS ]
C₄₅H₃₉ClN₇O₄Pol [ No CAS ]
C₄₇H₄₁N₆O₆Pol [ No CAS ]
C₄₅H₄₅N₈O₅Pol [ No CAS ]
C₄₄H₄₄N₉O₆Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ISOPROPYLAMIDE; at 60℃;Combinatorial reaction / High throughput screening (HTS);	Step 2. Catalytic amination of the solid supported 8-iodo-l-methyl-4,5-dihydro- lH-pyrazolo [4,3-h] quinazoline-3-carboxamide; <n="82"/>Using a 4 niL Argonaut Trident synthesizer cassette, 200 mg (0.11 mmol) of the resin from step 1 above, were charged into separate vials. To each of the reactor vials flushed with argon, finely divided potassium carbonate (0.15 g, 1.1 mmol), palladium acetate [Pd(OAc)2] (2.5mg, 0.011 mmol, 10%), (HK)-BINAP (6.8 mg, 0.011 mmol, 10%) and the corresponding amine (0.22 mmol, 2 equivalents) in degassed (argon) dimethyacetamide (2 mL) were added. The resulting mixture was agitated at 600C for 10 hours on the Argonaut Trident Automated Library Synthesizer (ALS) station. The Trident ALS station was programmed to continuously mechanically agitate the resin at 6O0C while a nitrogen gas "sparge" was incorporated to re-suspend the scarcely soluble potassium carbonate. Nitrogen gas sparging was incorporated once per hour, for a 30 second duration, throughout the 16-hour heating cycle.The resin was drained from the synthesis cocktail and washed using the Argonaut Trident External Agitation Thermal Unit (EATU) synthesis station with DMA (3 x 2 mL, 5 min.). The above catalytic amination cycle was repeated a second time using the previously described procedure.Upon completion of the second amination cycle, the resin was drained from the synthesis cocktail and washed using the Argonaut Trident EATU synthesis station with DMF (1 x 2 mL, 5 min.), with water (1 x 2 mL, 5 min.), with DMF/water (1 : 1) (3 x 2 mL, 5 min.), with DMF (3 x 2 mL, 5 min.), with methanol (3 x 2 mL, 5 min.) and with DCM (3 x 2 mL, 5 min.).

Reference： [1]Patent: WO2008/74788,2008,A1 .Location in patent: Page/Page column 80-81

15
[ 100-52-7 ]
[ 54705-91-8 ]
[ 1205612-03-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol at 20℃; for 48h; Molecular sieve;

Reference： [1]Cadogan; Clark, Bernard A. J.; Ford, Daniel; MacDonald, Ranald J.; MacPherson, Andrew D.; McNab, Hamish; Nicolson, Iain S.; Reed, David; Sommerville, Craig C. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5173 - 5183]

16
[ 883120-36-3 ]
[ 54705-91-8 ]
C₂₂H₁₆N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0℃;

Reference： [1]Location in patent: experimental part Kemnitzer, William; Sirisoma, Nilantha; Jiang, Songchun; Kasibhatla, Shailaja; Crogan-Grundy, Candace; Tseng, Ben; Drewe, John; Cai, Sui Xiong [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1288 - 1292]

17
[ 500549-35-9 ]
[ 54705-91-8 ]
7-nitro-N-(2-(1H-pyrazol-1-yl)-phenyl)-9-oxo-9H-fluorene-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0℃;

18
[ 591-50-4 ]
[ 54705-91-8 ]
[ 1202706-30-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 20 - 110℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Peng, Kuo-Fu; Chen, Chi-Tien [Dalton Transactions, 2009, # 44, p. 9800 - 9806]

19
[ 578-57-4 ]
[ 54705-91-8 ]
[ 1202706-28-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 20 - 110℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Peng, Kuo-Fu; Chen, Chi-Tien [Dalton Transactions, 2009, # 44, p. 9800 - 9806]

20
[ 33775-94-9 ]
[ 54705-91-8 ]
[ 1202706-29-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium phosphate; copper(l) iodide; <i>L</i>-proline In toluene at 20 - 110℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Peng, Kuo-Fu; Chen, Chi-Tien [Dalton Transactions, 2009, # 44, p. 9800 - 9806]

21
[ 1573-92-8 ]
[ 54705-91-8 ]
N-(2-(1H-pyrazol-1-yl)phenyl)-9-oxo-9H-fluorene-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 2-(1H-pyrazol-1-yl)aniline With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: 9-oxo-9H-fluorene-1-carboxylic acid In tetrahydrofuran at 0℃; for 1.03333h;	9 To a flame-dried 2-neck reaction flask charged with a magnetic stir bar, under argon, at room temperature was added NaH (60% mineral oil, 0.565 g, 14.1 mmol) and THF (47 mL). The gray suspension was cooled to O C and then 2-(lH-pyrazol-l-yl)-aniline (1.50 g, 9.42 mmol) was added, forming a green suspension. The suspension was stirred for 20 min, and 9-oxo-9H-fluorene-l-carbonyl chloride (2.28 g, 9.42 mmol) was added in small portions over 2 min. The brown suspension was stirred at O C for 1 h, equilibrated to room temperature, quenched with H2O (5 mL) and then the solvent was evaporated. The resulting yellow residue was diluted with EtOAc (500 mL), washed with H2O (3 x 40 mL), dried over MgSO4, filtered and concentrated to yield a yellow solid. Recrystallization of the yellow solid with EtOH (220 niL) yielded 2.15 g (63%) of the title compound as a brown solid: mp 164-1660C; 1H-NMR (CDCl3): 11.20 (br s, IH), 8.50 (d, J= 7.1 Hz, IH), 7.86-7.83 (m, 2H), 7.66-7.64 (m, IH), 7.61- 7.52 (m, 5H), 7.46-7.40 (m, 2H), 7.34-7.29 (m, 2H), 6.41 (t, J = 2.2 Hz, IH).

Reference： [1]Current Patent Assignee: IMMUNE PHARMACEUTICALS INC - WO2006/39356, 2006, A2 Location in patent: Page/Page column 35-36

22
[ 98-09-9 ]
[ 54705-91-8 ]
[ 1430586-20-1 ]
C₂₁H₁₇N₃O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 64% 2: 17%	With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	4.5. HNSO2PhHPzH To a flask containing 1-(2-aminophenyl)pyrazole (0.796g, 5.0mmol) in 15mL dichloromethane, a solution of benzenesulfonyl chloride (0.970g, 5.5mmol) in 15mL dichloromethane was added at room temperature. To this mixture solution, NEt3 (0.765mL, 5.5mmol) was added via syringe at 0°C. After one hour of stirring, all the volatiles were pumped off and the residue was extracted with toluene 5mL×3. Crude product was purified by column chromatography (hexane/ethyl acetate 3:1). The second band was collected to afford white solid (0.958g, 64.0%). The third band was collected to afford di-substituted side product, PzHN(SO2PhH)2, as white solid (0.375g, 17.0%). Data for HNSO2PhHPzH: Anal. Calc. for C15H13N3O2S: C, 60.18; H, 4.38; N, 14.04. Found: C, 59.74; H, 4.26; N, 13.64. 1H NMR (400MHz, CDCl3): δ (ppm) 10.09 (br, 1H, -NH), 7.77 (dd, J=8.0 & 1.4Hz, 1H, C6H5), 7.72 (d, J=2.0Hz, 1H, C6H5), 7.38 (m, 3H, C6H5), 7.27-7.33 (overlap, 2H, C6H5), 7.12-7.23 (overlap, 4H, C6H5), 6.33 (m, 1H, C6H5). 13C NMR (100MHz, CDCl3): δ (ppm) 138.7, 131.4, 129.8 (Cipso-C6H5), 141.0, 132.3, 129.3, 128.6, 127.8, 126.4, 126.1, 125.8, 121.7, 107.3 (CH-C6H5). Data for PzHN(SO2PhH)2: Anal. Calc. for C21H17N3O4S2: C, 57.39; H, 3.90; N, 9.56. Found: C, 57.20; H, 3.69; N, 9.15. NMR (400MHz, CDCl3): δ (ppm) 8.17 (m, 1H, C6H5), 7.84-7.87 (overlap, 4H, C6H5), 7.62-7.69 (overlap, 3H, C6H5), 7.58 (td, J=7.8 & 1.2Hz, 1H, C6H5), 7.47-7.51 (overlap, 5H, C6H5), 7.32 (m, 1H, C6H5), 6.95 (dd, J=8.0 & 1.4Hz, 1H, C6H5), 6.10 (t, J=2.0Hz, 1H, C6H5). 13C NMR (100MHz, CDCl3): δ (ppm) 140.7, 138.7, 127.7 (Cipso-C6H5), 141.2, 134.0, 132.6, 131.5, 131.4, 129.1, 128.7, 128.0, 127.8, 107.4 (CH-C6H5) [49]and[50].

Reference： [1]Chen, Chi-Tien; Liao, Chien-Hung; Peng, Kuo-Fu; Chen, Ming-Tsz; Huang, Tzu-Lun [Journal of Organometallic Chemistry, 2014, vol. 753, p. 9 - 19]

23
[ 98-59-9 ]
[ 54705-91-8 ]
[ 1379667-34-1 ]
C₂₃H₂₁N₃O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 67% 2: 7%	With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	4.6. HNSO₂Ph^MePz^H To a flask containing 1-(2-aminophenyl)pyrazole (0.796g, 5.0mmol) and toluenesulfonyl chloride (1.05g, 5.5mmol), 30mL dichloromethane were added at room temperature. To this reaction mixture, NEt3 (0.765mL, 5.5mmol) was added via syringe at 0°C. After one hour of stirring, all the volatiles were pumped off. The residue was extracted with toluene (5mL×3). Crude product was purified by column chromatography (hexane/ethyl acetate 3:1). The second band was collected to afford pale-white solid (1.05g, 67.0%). The third band was collected to afford di-substituted side product, PzHN(SO2PhMe)2, as white solid (0.165g, 7.0%). Data for HNSO2PhMePzH: Anal. Calc. for C16H15N3O2S: C, 61.32; H, 4.82; N, 13.41. Found: C, 61.60; H, 5.08; N, 13.50. 1H NMR (400MHz, CDCl3): δ (ppm) 10.04 (br, 1H, -NH), 7.73-7.77 (overlap, 2H, C6H5), 7.26-7.34 (overlap, 4H, C6H5), 7.14-7.20 (overlap, 2H, C6H5), 7.01 (d, J=8.4Hz, 2H, C6H5), 6.36 (m, 1H, C6H5), 2.30 (s, 3H, -CH3). 13C NMR (100MHz, CDCl3): δ (ppm) 143.1, 135.7, 131.0, 129.8 (Cipso-C6H5), 140.8, 129.2, 129.1, 127.6, 126.3, 125.8, 125.2, 121.6, 107.1 (CH-C6H5), 21.2 (-CH3). Data for PzHN(SO2PhMe)2: Anal. Calc. for C23H21N3O4S2: C, 59.08; H, 4.53; N, 8.99. Found: C, 59.05; H, 4.73; N, 8.40. 1H NMR (400MHz, CDCl3): δ (ppm) 8.20 (m, 1H, C6H5), 7.71 (d, J=8.4Hz, 4H, C6H5), 7.67 (dd, J=8.0 & 1.6Hz, 1H, C6H5), 7.52-7.58 (overlap, 2H, C6H5), 7.31 (m, 2H, C6H5), 7.26 (dd, J=8.0 & 0.4Hz, 4H, C6H5), 6.96 (d, J=8.4Hz, 1H, C6H5), 6.13 (m, 1H, C6H5), 2.46 (s, 6H, -CH3). 13C NMR (100MHz, CDCl3): δ (ppm) 145.1, 140.7, 135.9, 131.3 (Cipso-C6H5), 141.0, 132.6, 131.5, 129.3, 129.2, 127.9, 127.7, 107.3 (CH-C6H5), 21.6 (-CH3) [51].

Reference： [1]Chen, Chi-Tien; Liao, Chien-Hung; Peng, Kuo-Fu; Chen, Ming-Tsz; Huang, Tzu-Lun [Journal of Organometallic Chemistry, 2014, vol. 753, p. 9 - 19]

24
[ 773-64-8 ]
[ 54705-91-8 ]
[ 1388180-51-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	4.6. HNSO₂Ph^MePz^H General procedure: The procedure for the preparation of HNSO2PhTriMePzH was similar to that used for HNSO2PhMePzH but with 2-mesitylenesulfonyl chloride (1.20g, 5.5mmol) and 20mL dichloromethane. The second band was collected to afford white solid (0.96g, 56.0%). Anal. Calc. for C18H19N3O2S: C, 63.32; H, 5.61; N, 12.31. Found: C, 63.18; H, 5.49; N, 12.53. 1H NMR (400MHz, CDCl3): δ (ppm) 9.97 (br, 1H, -NH), 7.75 (d, J=1.2Hz, 1H, C6H5), 7.55 (dd, J=8.0 & 1.2Hz, 1H, C6H5), 7.51 (dd, J=2.4 & 0.4Hz, 1H, C6H5), 7.19-7.26 (overlap, 2H, C6H5), 7.13 (m, 1H, C6H5), 6.79 (br, 2H, C6H5), 6.40 (m, 1H, C6H5), 2.41 (s, 6H, o-CH3-Ph), 2.22 (s, 3H, p-CH3-Ph). 13C NMR (100MHz, CDCl3): δ (ppm) 142.1, 138.8, 133.4, 130.2, 130.1 (Cipso-C6H5), 141.0, 132.6, 131.5, 129.3, 129.2, 127.9, 127.7, 107.3 (CH-C6H5), 21.6 (-CH3).

Reference： [1]Chen, Chi-Tien; Liao, Chien-Hung; Peng, Kuo-Fu; Chen, Ming-Tsz; Huang, Tzu-Lun [Journal of Organometallic Chemistry, 2014, vol. 753, p. 9 - 19]

25
[ 349-88-2 ]
[ 54705-91-8 ]
[ 1542317-46-3 ]
[ 1542317-50-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 28% 2: 10%	With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	4.6. HNSO₂Ph^MePz^H General procedure: The procedure for the preparation of HNSO2PhFPzH was similar to that used for HNSO2PhMePzH but with 4-fluorobenzene-sulfonyl chloride (2.92g, 15mmol). Crude product was purified by column chromatography (hexane/ethyl acetate 5:1). The second band was collected to afford orange-red oil. The oil was triturated with ethanol to afford orange solid (1.33g, 28.0%). The third band was collected to afford di-substituted side product, PzHN(SO2PhF)2, as white solid (0.71g, 10.0%). Data for HNSO2PhFPzH: Anal. Calc. for C15H12FN3O2S: C, 56.77; H, 3.81; N, 13.24. Found: C, 56.80; H, 3.88; N, 12.96. 1H NMR (400MHz, CDCl3): δ (ppm) 10.10 (br, 1H, -NH), 7.74-7.79 (overlap, 2H, C6H5), 7.32-7.40 (overlap, 4H, C6H5), 7.17-7.27 (overlap, 2H, C6H5), 6.89 (t, J=8.4Hz, 2H, C6H5), 6.37 (br, 1H, C6H5). 13C NMR (100MHz, CDCl3): δ (ppm) 166.0, 163.4, 134.6, 131.4 (Cipso-C6H5), 141.0, 129.2, 129.1, 129.0, 127.9, 126.4, 126.1, 121.6, 115.9, 115.7, 107.3 (CH-C6H5). Data for PzHN(SO2PhF)2: Anal. Calc. for C21H15F2N3O4S2: C, 53.05; H, 3.18; N, 8.84. Found: C, 53.51; H, 3.34; N, 9.07. 1H NMR (400MHz, CDCl3): δ (ppm) 8.12 (m, 1H, C6H5), 7.87-7.90 (overlap, 4H, C6H5), 7.57-7.66 (overlap, 2H, C6H5), 7.51 (d, J=1.6Hz, 1H, C6H5), 7.35 (m, 1H, C6H5), 7.14-7.18 (overlap, 4H, C6H5), 6.97 (dd, J=8.0 & 1.6Hz, 1H, C6H5), 6.16 (m, 1H, C6H5). 13C NMR (100MHz, CDCl3): δ (ppm) 167.2, 164.6, 140.6, 134.6, 127.7 (Cipso-C6H5), 141.3, 132.5, 132.3, 132.2, 131.7, 131.4, 128.2, 128.0, 116.2, 116.0, 107.5 (CH-C6H5).

Reference： [1]Chen, Chi-Tien; Liao, Chien-Hung; Peng, Kuo-Fu; Chen, Ming-Tsz; Huang, Tzu-Lun [Journal of Organometallic Chemistry, 2014, vol. 753, p. 9 - 19]

26
[ 349-88-2 ]
[ 54705-91-8 ]
[ 1542317-50-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In tetrahydrofuran at 0 - 50℃; for 1h; Inert atmosphere;	4.9. Pz^HN(SO₂Ph^F)₂ To a flask containing 1-(2-aminophenyl)pyrazole (0.159g, 1.0mmol) and 4-fluorobenzene-sulfonyl chloride (0.428g, 1.0mmol), 30mL THF were added at room temperature. To this reaction mixture, NEt3 (0.31mL, 2.2mmol) was added via syringe at 0°C. The reaction mixture was warmed up to 50°C. After one hour of stirring, all the volatiles were pumped off. The residue was extracted with toluene (5mL×3). Crude product was purified by column chromatography (hexane/ethyl acetate 3:1). The second band was collected to afford white solid (0.357g, 75.0%). 1H NMR (400MHz, CDCl3): δ (ppm) 8.12 (m, 1H, C6H5), 7.87-7.90 (overlap, 4H, C6H5), 7.57-7.66 (overlap, 2H, C6H5), 7.51 (d, J=1.6Hz, 1H, C6H5), 7.35 (m, 1H, C6H5), 7.14-7.18 (overlap, 4H, C6H5), 6.97 (dd, J=8.0 & 1.6Hz, 1H, C6H5), 6.16 (m, 1H, C6H5). 13C NMR (100MHz, CDCl3): δ (ppm) 167.2, 164.6, 140.6, 134.6, 127.7 (Cipso-C6H5), 141.3, 132.5, 132.3, 132.2, 131.7, 131.4, 128.2, 128.0, 116.2, 116.0, 107.5 (CH-C6H5).

Reference： [1]Chen, Chi-Tien; Liao, Chien-Hung; Peng, Kuo-Fu; Chen, Ming-Tsz; Huang, Tzu-Lun [Journal of Organometallic Chemistry, 2014, vol. 753, p. 9 - 19]

27
[ 54705-91-8 ]
[ 82417-45-6 ]
[ 1571072-03-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With pyridine at 20℃; for 18h;

Reference： [1]Miah, Afjal H.; Copley, Royston C. B.; O'Flynn, Daniel; Percy, Jonathan M.; Procopiou, Panayiotis A. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 11, p. 1779 - 1792]

28
[ 288-13-1 ]
[ 615-43-0 ]
[ 54705-91-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With copper diacetate; sodium hydroxide; 3-(diphenylphosphino)propionic acid In 1,4-dioxane at 100℃; for 24h; Sealed tube;	Procedure for N-arylation of 1H-pyrazole: General procedure: Cu(OAc)2 (0.03mmol), L2 (0.06mmol), aryl idione or bromide (0.5mmol), 1H-pyrazole (0.75mmol), NaOH (1mmol), and 1,4-dioxane (1mL) was added into a 5mL tube, then sealed. The mixture was stirred at 100°C for certain time. After cooling to room temperature, the mixture was quenched with 10mL H2O and extracted with EtOAc (3×20mL). The combined EtOAc extracts were dried with anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE/EtOAc, as the eluent, to afford the desired products.

Reference： [1]Liu, Ya-Shuai; Liu, Yan; Ma, Xiao-Wei; Liu, Ping; Xie, Jian-Wei; Dai, Bin [Chinese Chemical Letters, 2014, vol. 25, # 5, p. 775 - 778]

29
1-(2-bromophenyl)pyrazole [ No CAS ]
[ 54705-91-8 ]
C₁₈H₁₅N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 1-(2-bromophenyl)pyrazole; 2-(1H-pyrazol-1-yl)aniline With copper(l) iodide; caesium carbonate In 1,4-dioxane for 15h; Inert atmosphere; Reflux; Schlenk technique; Stage #2: In ethanol for 0.0333333h; Reflux;

Reference： [1]Hewage, Jeewantha S.; Wanniarachchi, Sarath; Morin, Tyler J.; Liddle, Brendan J.; Banaszynski, Megan; Lindeman, Sergey V.; Bennett, Brian; Gardinier, James R. [Inorganic Chemistry, 2014, vol. 53, # 19, p. 10070 - 10084]

30
[ 141573-96-8 ]
[ 54705-91-8 ]
N-(2-(1H-pyrazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0℃; for 0.5h;

Reference： [1]Du, Shijie; Tian, Zaimin; Yang, Dongyan; Li, Xiuyun; Li, Hong; Jia, Changqing; Che, Chuanliang; Wang, Mian; Qin, Zhaohai [Molecules, 2015, vol. 20, # 5, p. 8395 - 8408]

31
[ 124-38-9 ]
[ 54705-91-8 ]
[ 114722-60-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium t-butanolate In diethylene glycol dimethyl ether at 140℃; for 24h; Glovebox; Schlenk technique;

Reference： [1]Zhang, Zhen; Liao, Li-Li; Yan, Si-Shun; Wang, Lei; He, Yun-Qi; Ye, Jian-Heng; Li, Jing; Zhi, Yong-Gang; Yu, Da-Gang [Angewandte Chemie - International Edition, 2016, vol. 55, # 25, p. 7068 - 7072][Angew. Chem., 2016, vol. 128, p. 7184 - 7188]

32
N-(2-(1H-pyrazol-1-yl)phenyl)benzamide [ No CAS ]
[ 162787-61-3 ]
[ 54705-91-8 ]