Name: 6165-76-0|Propargyl p-toluenesulfonate|95%
Brand: Ambeed
SKU: A321954
Price: 13.0 USD
Availability: InStock
Rating: 96 (35 reviews)

1
[ 107-19-7 ]
[ 98-59-9 ]
[ 6165-76-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide In diethyl ether; water monomer at 0 - 20℃; for 17h;
96%	With potassium hydroxide In diethyl ether at -5 - 20℃;
95%	With potassium hydroxide In diethyl ether at -5 - 0℃; for 0.5h;

94%	With sodium hydroxide In propan-2-one for 0.25h; Inert atmosphere;
91%	With N-Trimethylamine hydrochloride; potassium carbonate at 0 - 5℃; for 1h;
91%	With potassium hydroxide In diethyl ether at 0 - 20℃; for 2h;	2. Synthesis of electrophiles General procedure: Add potassium hydroxide (2.37 g, 42.3 mmol), sulfuryl chloride (10.4 mmol) and ether(20 ml) in a single mouthed flask under ice water bath, then slowly add propargyl alcohol (0.46ml, 8.46 mmol). After stirring at room temperature, TLC showed that the raw materialdisappeared, washed and extracted by DCM. The combined organic layers were dried overMgSO4, concentrated in vacuo and the crude product was purified by silica gel columnchromatography.
89%	With pyridine at 0 - 25℃; for 5h;	1 Example 1: Add 0.050 mol of p-toluenesulfonyl chloride and 40 mL of pyridine to the reaction flask at 0 to 5 ° C.Add 0.055 mol of propargyl alcohol dropwise with stirring,After the addition was completed, the mixture was stirred for 4 hours at 0 to 5 ° C, and then heated to 25 ° C for 1 hour.Add 50 mL of water to the reaction system,It was extracted with 3 × 20 mL of dichloromethane. The organic phase was washed with 6M hydrochloric acid, saturated sodium bicarbonate, and 20% saline in this order.Dried over anhydrous magnesium sulfate,After the organic phase is removed from the solvent, propargyl p-toluenesulfonate is obtained,Yield: 89%.
85%	With potassium hydroxide In diethyl ether at 0℃; for 0.5h;
85%	With potassium hydroxide In diethyl ether at -10℃;
85%	With benzyl-triethyl-ammonium chloride; sodium hydroxide In tetrahydrofuran; water monomer at 0℃; for 1h;
84%	With sodium hydroxide In diethyl ether at 0 - 20℃; Inert atmosphere;	Synthesis of propargyl tosylate A 2 L round bottom flask equipped with a mechanical stirrer was charged with 58 mL (1.0 mol) of propargyl alcohol, 250 g (1.30 mol) of tosyl chloride and 1000 mL of diethyl ether under nitrogen. The resulting reaction mixture was cooled in an ice bath, and NaOH pellets (200 g, 5.00 mol) were added to the solution in 6 portions at 0 °C under vigorous stirring. The resulting mixture was continually stirred overnight at room temperature. The suspension was poured into cold water and the resulting aqueous layer was extracted with ether (2 × 250 mL). The ether layer was combined, dried over anhydrous Na2SO4 and concentrated. Pure propargyl tosylate was obtained as a dark liquid [30,47] in 84.0% yield (185 g) by drying under high vacuum (Caution: gloves are required when handling propargyltosylate).
77%	Stage #1: Prop-2-ynyl alcohol With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 4-methylbenzenesulfonyl chloride In tetrahydrofuran; hexane at -80℃; for 48h;
70%	With potassium carbonate; 1-hexadecyl-1H-imidazole In water monomer at 25℃; for 4h;
41%	With potassium hydroxide In diethyl ether at 20℃; for 0.5h; Cooling with ice;	Procedure for the preparation of Alkyne linkers 14 and 15: General Procedure: Based upon the preparation by Dickshats et al., 4 to an ice-cold solution of propargyl alcohol 15(1.00g, 1 eq) and tosyl chloride (4.09 g, 1.2 eq) in ether was added potassium hydroxide (12.0 g, 10 eq). The solution stirred at room temperature for thirty minutes, then poured into ice water. The organic layer was removed and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and dried with sodium sulfate, and the crude product purified by flash chromatography(hexanes/DCM, 1/1) to produce 14 as a clear oil (1.53g, 41%). 1H NMR (300 MHz, CDCl3) 7.82 (d, J= 8.3, 2H), 7.35 (d, J = 8.0, 2H), 4.78 4.65 (m, 2H), 2.47 (dd, J = 3.9, 3.3, 4H). 13C NMR (75 MHz,CDCl3) 145.4, 133.1, 130.1, 128.3, 77.5, 75.6, 57.5, 21.9.
	With sodium hydroxide
	With potassium hydroxide
	With potassium hydroxide In diethyl ether
	With potassium hydroxide 1.) ether, -5 deg C, 20 min; 2.) ether, 0 deg C, 3 h; Yield given. Multistep reaction;
	With potassium hydroxide In diethyl ether at 0℃;
	With n-butyllithium In diethyl ether
	With potassium hydroxide at 0℃; for 0.5h;
	With potassium hydroxide at -50℃;
	With triethylamine In tetrahydrofuran at 0 - 20℃;
	With potassium hydroxide In dichloromethane at 0℃; for 1h;
	With potassium hydroxide In tetrahydrofuran at -10 - 20℃; for 5h;	General Procedure for the Synthesis of Prop-2-ynyl-4-methyl Benzenesulfonate (5) To a solution of propargyl alcohol (53.5 mmol) in THF (40 mL), potassium hydroxide (196.1 mmol) was added. To the stirred solution p-toulenesulphonyl chloride (62.2 mmol) was added in ten equal portions at -10 °C during an hour. After complete addition, reaction mixture was warmed to room temperature and stirred for 4 h. On completion,THF was evaporated under vacuum. Then mixture was (9.5: 0.5). The combined organic layers were dried using MgSO4, filtered and dissolved in distilled water and extracted with ethyl acetate, concentrated to afford brown viscous liquid in 75%. 1H NMR (300 MHz, CDCl3): 7.81 (2H, d, J = 8.4 Hz, ArH), 7.34 (2H, d, J = 8.4 Hz, ArH), 4.68 (2H, d, J= 2.7 Hz, CH2), 2.45 (4H, t + s, CH3, CC-H); MS (EI) m/z (rel. abund. %): 210 (M+, 7), 155 (36), 118 (44), 91 (100).
	With potassium hydroxide In diethyl ether at -5 - 20℃; for 5h; Sealed tube; Inert atmosphere;
	With sodium hydroxide In diethyl ether for 17h;
	With potassium carbonate In water monomer at 25℃; for 0.166667h; Sonication; Green chemistry;	General procedure for the one-pot synthesis of compounds (5a-j) General procedure: General procedure for the one-pot synthesis of compounds (5a-j): To solution of propargyl alcohol 2a (1 mmol) or propargylamine 2b (1 mmol) and K2CO3 (1 mmol) in H2O (10 mL) was added R1SO2Cl 1 (1.1 mmol) (R1=Me (1a); R1=Ph (1b); R1= p-CH3-C6H4 (1c)) dropwise. The reaction mixture was stirred for 2h (or sonicated for 10 min) at 25°C. Then the aromatic aldehyde 3a-f (1 mmol) and hydroxylamine hydrochloride 4 (1.2 mmol) and NaDCC (0.5 mmol) were added successively and the mixture was sonicated according to the time reported in Table 3 using the ultrasonic bath (47kHz). The completion of the reaction was monitored by TLC. The mixture was extracted with CH2Cl2 (20 mL x 2). The organic phase was washed with water (20 mL) and saturated brine solution (20 mL), dried over MgSO4 and concentrated in vacuum to give the crude products, which were purified by recrystallisation in EtOH to afford the pure adducts 5a-j
	With sodium hydroxide In diethyl ether; water monomer at 20℃; for 17h;
	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Soltani Rad, Mohammad Navid; Behrouz, Somayeh; Mohammadtaghi-Nezhad, Javad; Zarenezhad, Elham; Agholi, Mahmoud [Applied Organometallic Chemistry, 2019, vol. 33, # 4]
[2]Srinivasan, Rajavel; Uttamchandani, Mahesh; Yao, Shao Q. [Organic Letters, 2006, vol. 8, # 4, p. 713 - 716]
[3]Aidhen; Braslau [Synthetic Communications, 1994, vol. 24, # 6, p. 789 - 797]
[4]Karmis, Rebecca E.; Carrara, Serena; Baxter, Amy A.; Hogan, Conor F.; Hulett, Mark D.; Barnard, Peter J. [Dalton Transactions, 2019, vol. 48, # 27, p. 9998 - 10010]
[5]Tanabe, Yoo; Yamamoto, Hitomi; Yoshida, Yoshihiro; Miyawaki, Takashi; Utsumi, Naoka [Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 1, p. 297 - 300]
[6]Xie, Li-Jun; Lin, Cui-Lian; Liu, Li; Cheng, Liang [Chinese Chemical Letters, 2022, vol. 33, # 3, p. 1563 - 1566]
[7]Current Patent Assignee: ANHUI UNIVERSITY - CN110776475, 2020, A Location in patent: Paragraph 0025; 0026
[8]Dickschat, Jeroen S.; Reichenbach, Hans; Wagner-Doebler, Irene; Schulz, Stefan [European Journal of Organic Chemistry, 2005, # 19, p. 4141 - 4153]
[9]Location in patent: experimental part Bertoldo, Monica; Nazzi, Samuele; Zampano, Giovanni; Ciardelli, Francesco [Carbohydrate Polymers, 2011, vol. 85, # 2, p. 401 - 407]
[10]Location in patent: experimental part Isaacman, Michael J.; Barron, Kathryn A.; Theogarajan, Luke S. [Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 12, p. 2319 - 2329]
[11]Zhang, Quanxuan; Ren, Hong; Baker, Gregory L. [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1365 - 1371]
[12]Hastings, Courtney J.; Fiedler, Dorothea; Bergman, Robert G.; Raymond, Kenneth N. [Journal of the American Chemical Society, 2008, vol. 130, # 33, p. 10977 - 10983]
[13]Asano, Keisuke; Matsubara, Seijiro [Organic Letters, 2009, vol. 11, # 8, p. 1757 - 1759]
[14]Findlay, Brandon; Zhanel, George G.; Schweizer, Frank [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1499 - 1503]
[15]Zeile; Meyer [Chemische Berichte, 1942, vol. 75, p. 356,360] Current Patent Assignee: Schlichting; Klager - US2340701, 1941, A Reppe et al. [Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 65]
[16]Prib,O.A.; Malinovskii,M.S. [Journal of general chemistry of the USSR, 1963, vol. 33, p. 647 - 650][Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 653 - 657]
[17]Vizgert,R.V. et al. [Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 914 - 919][Zhurnal Organicheskoi Khimii, 1969, vol. 5, p. 926 - 928]
[18]Audin, Patrick; Doutheau, Alain; Gore, Jacques [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 7-8, p. 297 - 306]
[19]Oh, Hyuck Keun; Cho, In Ho; Jin, Min Jeong; Lee, Ikchoon [Journal of Physical Organic Chemistry, 1994, vol. 7, p. 629 - 633]
[20]Dunn, Michael J.; Jackson, Richard F. W.; Pietruszka, Joerg; Turner, Debra [Journal of Organic Chemistry, 1995, vol. 60, # 7, p. 2210 - 2215]
[21]Mamane, Victor; Gress, Tobias; Krause, Helga; Fuerstner, Alois [Journal of the American Chemical Society, 2004, vol. 126, # 28, p. 8654 - 8655]
[22]Jonasson; Horvath; Backvall [Journal of the American Chemical Society, 2000, vol. 122, # 40, p. 9600 - 9609]
[23]Location in patent: experimental part Yin, Yanzhen; Huang, Xin; Lv, Chunyan; Wang, Liang; Yu, Shuangjiang; Luo, Quan; Xu, Jiayun; Liu, Junqiu [Macromolecular Bioscience, 2010, vol. 10, # 12, p. 1505 - 1516]
[24]Konda, Saidulu; Rao, Pallavi; Oruganti, Srinivas [RSC Advances, 2014, vol. 4, # 109, p. 63962 - 63965]
[25]Khan, Maria Aqeel; Saleem, Aliyan; Ghouri, Nida; Hameed, Abdul; Iqbal Choudhary; Basha, Fatima Z. [Letters in drug design and discovery, 2015, vol. 12, # 7, p. 597 - 606]
[26]Ayres, James N.; Williams, Matthew T.J.; Tizzard, Graham J.; Coles, Simon J.; Ling, Kenneth B.; Morrill, Louis C. [Organic Letters, 2018, vol. 20, # 17, p. 5282 - 5285]
[27]Behrouz, Somayeh; Soltani Rad, Mohammad Navid; Taghavi Shahraki, Bahareh; Fathalipour, Mohammad; Behrouz, Marzieh; Mirkhani, Hossein [Molecular Diversity, 2019, vol. 23, # 1, p. 147 - 164]
[28]Talha, Aicha; Tachallait, Hamza; Benhida, Rachid; Bougrin, Khalid [Tetrahedron Letters, 2021, vol. 81]
[29]Behrouz, Somayeh; Mohammad-Javadi, Mehdi; Soltani Rad, Mohammad Navid; Zarenezhad, Elham [Molecular Diversity, 2021]
[30]Shao, Liang; Yang, Fan; Su, Yangqing; Li, Weijia; Zhang, Jihong; Xu, Huan; Huang, Boxuan; Sun, Mengsi; Mu, Yu; Zhang, Yuan; Yu, Fei [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 11, p. 1759 - 1765]

2
[ 6165-76-0 ]
[ 1666-19-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid; mercury(II) sulfate In methanol; water at 60℃; for 2h;
	With sulfuric acid; mercury(II) sulfate

Reference： [1]Dickschat, Jeroen S.; Reichenbach, Hans; Wagner-Doebler, Irene; Schulz, Stefan [European Journal of Organic Chemistry, 2005, # 19, p. 4141 - 4153]
[2]Prib,O.A.; Yasinskii,I.M. [Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 342 - 344][Zhurnal Organicheskoi Khimii, 1971, vol. 7, # 2, p. 348 - 350]

3
[ 6165-76-0 ]
[ 86953-79-9 ]
[ 233595-58-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: tert-butyl pyrrolidine-1-carboxylate With sec.-butyllithium; (-)-sparteine In diethyl ether at -78℃; Stage #2: In tetrahydrofuran at -55℃; for 0.75h; Stage #3: propargyl p-toluenesulfonate
83%	Stage #1: tert-butyl pyrrolidine-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: In tetrahydrofuran at -78℃; for 0.75h; Stage #3: propargyl p-toluenesulfonate In tetrahydrofuran at -78 - 20℃; for 3h;

Reference： [1]Dieter, R. Karl; Nice, Lois E. [Tetrahedron Letters, 1999, vol. 40, # 23, p. 4293 - 4296]
[2]Dieter, R. Karl; Chen, Ningyi; Yu, Huayun; Nice, Lois E.; Gore, Vinayak K. [Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 2109 - 2119]

4
[ 2517-76-2 ]
[ 6165-76-0 ]
[ 82430-88-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 3-iodopropanenitrile With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 35℃; for 12h; Stage #2: With lithium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #3: propargyl p-toluenesulfonate In tetrahydrofuran at -40 - 20℃; Further stages.;
	Stage #1: 3-iodopropanenitrile With zinc Stage #2: Stage #3: propargyl p-toluenesulfonate

Reference： [1]Jonasson; Horvath; Backvall [Journal of the American Chemical Society, 2000, vol. 122, # 40, p. 9600 - 9609]
[2]Jonasson, Catrin; Karstens, Willem F. J.; Hiemstra, Henk; Bäckvall, Jan-E. [Tetrahedron Letters, 2000, vol. 41, # 10, p. 1619 - 1622]

5
[ 6165-76-0 ]
[ 161529-19-7 ]
[ 354988-07-1 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 4904 - 4914

6
[ 6165-76-0 ]
[ 13170-43-9 ]
[ 18301-63-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) cyanide; lithium chloride In diethyl ether at 20℃; for 17h;
3.6 g	Stage #1: (trimethylsilyl)methylmagnesium chloride With lithium chloride In diethyl ether for 0.666667h; Stage #2: propargyl p-toluenesulfonate In diethyl ether at -78 - 20℃; for 17h;

Reference： [1]Mentink, Gertjan; Van Maarseveen, Jan H.; Hiemstra, Henk [Organic Letters, 2002, vol. 4, # 20, p. 3497 - 3500]
[2]Mamane, Victor; Gress, Tobias; Krause, Helga; Fuerstner, Alois [Journal of the American Chemical Society, 2004, vol. 126, # 28, p. 8654 - 8655]

7
[ 6165-76-0 ]
[ 38527-59-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With carbon monoxide; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 0℃; for 30h;

Reference： [1]Nakamura, Masaki; Yamane, Motoki; Sakurai, Hidehiro; Narasaka, Koichi [Heterocycles, 2003, vol. 59, # 1, p. 333 - 345]

8
[ 6165-76-0 ]
[ 14297-34-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With carbon monoxide; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 0℃; for 30h;

Reference： [1]Nakamura, Masaki; Yamane, Motoki; Sakurai, Hidehiro; Narasaka, Koichi [Heterocycles, 2003, vol. 59, # 1, p. 333 - 345]

9
[ 6165-76-0 ]
[ 17113-31-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With carbon monoxide; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 0℃; for 30h;

Reference： [1]Nakamura, Masaki; Yamane, Motoki; Sakurai, Hidehiro; Narasaka, Koichi [Heterocycles, 2003, vol. 59, # 1, p. 333 - 345]

10
[ 6165-76-0 ]
[ 17113-32-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With carbon monoxide; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 0℃; for 30h;

Reference： [1]Nakamura, Masaki; Yamane, Motoki; Sakurai, Hidehiro; Narasaka, Koichi [Heterocycles, 2003, vol. 59, # 1, p. 333 - 345]

11
[ 6165-76-0 ]
[ 100191-85-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With carbon monoxide; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 0℃; for 30h;

Reference： [1]Nakamura, Masaki; Yamane, Motoki; Sakurai, Hidehiro; Narasaka, Koichi [Heterocycles, 2003, vol. 59, # 1, p. 333 - 345]

12
[ 6165-76-0 ]
tetramethylammonium pentacarbonyl(benzoyl)chromate [ No CAS ]
[ 17113-33-6 ]

Reference： [1]Heterocycles,2003,vol. 59,p. 333 - 345

13
[ 6165-76-0 ]
[ 4466-24-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With carbon monoxide; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 0℃; for 30h;

Reference： [1]Nakamura, Masaki; Yamane, Motoki; Sakurai, Hidehiro; Narasaka, Koichi [Heterocycles, 2003, vol. 59, # 1, p. 333 - 345]

14
[ 95-57-8 ]
[ 6165-76-0 ]
[ 17061-92-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2011 - 2029

15
[ 6165-76-0 ]
[ 105-53-3 ]
[ 17920-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile for 24h; Heating / reflux;	2-Propargyl Malonic Acid Diethyl Ester; Diethyl malonate (10 g, 62.5 mmol), propargyl tossylate (13.1 g, 62.5 mmol) and andydrous K2CO3 (25.8 g, 187.5 mmol) were added to 100 mL of acetonitrile and refluxed for 24 h. The reaction mixture was cooled, concentrated and the residue was added to water to dissolve the excess K2CO3. The compound was extracted in ethyl acetate and the organic layer was washed with water, dried over Na2SO4 (anhydrous) and evaporated under vacuum. The pure compound was obtained by vacuum distillation.1H NMR (CDCI3, 400 MHz): δ 1.29 (t, 6H), 2.02 (t, 1H), 2.78 (dd, 2H), 3.56 (t, 1 H), 4.19-4.27 (m, 4H). 13C NMR (CDCI3, 100 MHz): 14.1, 18.4, 51.2, 61.8, 70.4, 80.0, 167.9.

Reference： [1]Current Patent Assignee: INDIAN INSTITUTES OF TECHNOLOGY - WO2006/117800, 2006, A2 Location in patent: Page/Page column 16

16
[ 6906-32-7 ]
[ 6165-76-0 ]
[ 1041847-71-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	In acetonitrile at 5℃; for 48h; Inert atmosphere;

Reference： [1]Hastings, Courtney J.; Fiedler, Dorothea; Bergman, Robert G.; Raymond, Kenneth N. [Journal of the American Chemical Society, 2008, vol. 130, # 33, p. 10977 - 10983]

17
[ 6165-76-0 ]
[ 10277-74-4 ]
[ 136236-51-6 ]

Yield	Reaction Conditions	Operation in experiment
		(R)-I -Indanamine (1 eq) was taken in dry THF (3 vol) and to the cooled reaction mixture, DBU (1.5 eq) was added dropwise. The reaction mixture was stirred for 1 hour at 0-5C. Propargyl tosylate (1.5 eq) was added dropwise at 0-5C and the mixture stirred for 2 hours at 20-25C. After completion of the reaction, the THF was removed under vacuum and water (3 vol) was added followed by 10% aqueous NaOH (10 vol) and the mixture was stirred for 15 minutes. Extraction was done with DCM, followed by washing with 10% aqueous NaOH and water. The DCM was removed under vacuum at 4O0C to afford rasagiline base.
		R)-1-Aminoindan (1 equivalent) was dissolved in dry THF (3 vol) and cooled to 0-50C. DBU (1.5 equivalents) was added slowly and the resultant mixture stirred for 30 minutes before propargyl tosylate (1.25 equivalents) was added dropwise. The reaction mixture was stirred for 4 hours at 15-200C. After completion of the reaction, the THF was removed under vacuum and water (3 vol) added. The product was extracted with DCM (3 x 3 vol), <n="15"/>followed by washing with 10% aqueous NaOH (2 x 3 vol) and water (2 x 3 vol). The DCM was removed under vacuum at 400C to obtain the product as a light yellow oil.Molar yield = 80-82% Chemical purity = 64.33% (measured by HPLC)

Reference： [1]Patent: WO2010/13048,2010,A1 .Location in patent: Page/Page column 9-10
[2]Patent: WO2009/147432,2009,A1 .Location in patent: Page/Page column 13 - 14

18
[ 6165-76-0 ]
[ 1195110-34-9 ]
[ 1195110-33-8 ]
[ 1195110-35-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 25%	With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Reflux; Inert atmosphere;
1: 30% 2: 25%	Stage #1: 4,4'-(5,5-difluoro-1,9-diphenyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,5,2]triazaborinine-3,7-diyl)diphenol With sodium hydride In tetrahydrofuran Stage #2: propargyl p-toluenesulfonate In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Reflux;	2.A Compound 6 (75 mg, 0.14 mmol) and NaH (60% oil dispersion) (12 mg, 0.52 mmol) were stirred in dry THF (8 mL) and treated with propargyltoluolsulfonate (12 mg, 0.31 mmol) at 0 °C under N2. The reaction was warmed to rt and then heated under reflux for 3 h. The reaction mixture was cooled and partitioned between EtOAc (10 mL) and brine (20 mL). The organic layer was separated, dried over sodium sulfate and the solvent removed under reduced pressure. Purification by column chromatography on silica eluting with C6Hi2/EtOAc (4: 1) first eluted compound 7 (21 mg, 25%) 166-169 °C followed by the desired product eluted with C6H12/EtOAc (3:2) 2 as a red metallic solid (25 mg, 30%, m.p. 82-84 °C ).Analysis for 21H NMR (300 MHz, CDC13): δ 8.09-7.99 (m, 8H), 7.47-7.38 (m, 6H), 7.07 (d, J = 8.7 Hz, 2H), 7.02 (s, 2H), 6.88 (d, J = 8.6 Hz, 2H), 5.6 (bs, 1H), 4.75 (s, 2H), 2.55 (s, 1H). 13C NMR (125 MHz, CDC13): δ 159.8, 158.7, 158.4, 157.7, 145.5, 145.2, 143.5, 143.1, 132.4,132.3, 131.8, 131.5, 131.4, 131.3, 129.3, 129.3, 129.2, 128.5, 125.0, 124.1, 118.8, 118.5, 115.8, 115.0, 78.0, 76.0, 55.9. IR (KBr disc): 3502, 1603 cm-1. ES-MS: m/z 568.4, [M + H]+. HRMS [M + H]+: 568.2034, C35H25BF2N302 requires 568.2008.Analysis for 71H NMR (300 MHz, CDC13): δ 8.12-8.07 (m, 8H), 7.49-7.42 (m, 6H), 7.06 (d, J = 9.1 Hz, 2H), 7.02 (s, 2H), 4.79 (s, 4H), 2.58 (s, 2H). 13C NMR (125 MHz, CDC13): δ 159.8, 158.1,145.4, 143.4, 132.4, 131.6, 131.5, 129.2, 128.5, 124.9, 118.7, 115.0, 78.0, 76.0, 55.8. IR (KBr disc): 1601, 1504 cm-1. ES-MS: m/z 606.2, [M + H]+. HRMS [M + H]+: 606.2135,C38H27BF2N302 requires 606.2164.

Reference： [1]Murtagh, Julie; Frimannsson, Daniel O.; O'Shea, Donal F. [Organic Letters, 2009, vol. 11, # 23, p. 5386 - 5389]
[2]Current Patent Assignee: ROYAL COLLEGE OF SURGEONS IN IRELAND - WO2011/48217, 2011, A1 Location in patent: Page/Page column 21-22

19
[ 22362-66-9 ]
[ 6165-76-0 ]
[ 1196517-03-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin; potassium carbonate In acetonitrile for 6h; Reflux;

Reference： [1]Tan, Lay Pheng; Wu, Hao; Yang, Peng-Yu; Kalesh, Karunakaran A.; Zhang, Xiaohua; Hu, Mingyu; Srinivasan, Rajavel; Yao, Shao Q. [Organic Letters, 2009, vol. 11, # 22, p. 5102 - 5105]

20
[ 6165-76-0 ]
[ 875-59-2 ]
[ 1196517-02-8 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5102 - 5105

21
[ 6165-76-0 ]
[ 426263-16-3 ]
3-methyl-3-((prop-2-ynyloxy)methyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methyl-3-(hydroxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: propargyl p-toluenesulfonate In tetrahydrofuran at 5 - 10℃;	3-methyl-3-((prop-2-ynyloxy)methyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine; To a suspension of NaH (600 mg, 15 mmol) in dry THF (10 mL), the (3-methyl-3,4-dihydro-2H- thieno[3,4-b][1 ,4]dioxepin-3-yl)-methanol (2 gm, 10 mmol) was added followed by addition of DABCO (1.12 mg, 0.01 mmol). The mixture was allowed to stir at room temperature for 15 minutes. The mixture was cooled to 5-10 0C using an ice bath and propargyl tosylate (2.52 gm, 12 mmol) was added drop wise to the reaction mixture. The mixture was allowed to stir overnight and quenched in water. The product was extracted in ethylacetate, washed in water dried over sodium sulphate and evaporated. This resulted a viscous oil which was purified by column chromatography (silica, eluant:hexane and ethyl acetate) resulting the pure propargyl functionalized ProDOT as demonstrated with NMR, Mass and elemental analysis. EPO 1H NMR (CDCI3): 0.99 (s, 3H), 2.43 (t, J = 2 Hz, 1 H), 3.59 (s, 2H), 3.72 (d, J = 11.6 Hz)1 4.03 (d, J = 11.6 Hz, 2H), 4.17 (d, J = 2.4 Hz), 6.48 (s, 2H). 13C NMR (CDCI3): 17.4, 43.2, 58.9, 72.6, 74.7, 76.8, 79.7, 105.7, 149.9.

Reference： [1]Current Patent Assignee: INDIAN INSTITUTES OF TECHNOLOGY - WO2006/117800, 2006, A2 Location in patent: Page/Page column 12-13

22
[ 10431-98-8 ]
[ 6165-76-0 ]
[ 1004550-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: propargyl p-toluenesulfonate With sodium bromide In acetonitrile at 25℃; for 3 - 4h; Stage #2: 2-ethyl-4,5-dihydrooxazole In acetonitrile at 25℃; for 18h;	2; 3 Example 2: N-Propargyl-2-Ethyl-2-Oxazolinium Bromide from the Finkelstein Reaction of Propargyl Tosylate and Sodium Bromide; To a 25-tnL round bottom flask containing a stir bar and flame - dried under N2 was added propargyl tosylate (1.0 g, 4.76 mmol), sodium bromide (SOO mg, 4.86 mmol) and 10 mL of anhydrous acetonitrile. This mixture was stirred at 25°C. The mixture was clear initially, but formed a slightly turbid mixture after 3 h. To this mixture was added, via Pasteur pipet, freshly distilled 2-ethyl-2-oxazoline (472 mg, 4.76 mmol). This mixture was stirred at 25°C for 18 h to give a white mixture/suspension with no observable NaBr remaining in the mixture.A MALDI - TOF mass spectrum of this mixture showed a peak at 136 amu for the desired N-propargyl-2- ethyl-2-oxazolinium bromide cation.The following reaction scheme illustrates this process.; Example 3: Reaction of N-Propargyl-2-Ethyl-2-OxazoIinium Bromide with Ethyl 1- piperazine carboxylate; To a 25 -mL round bottom flask containing a stir bar and flame - dried under N2 was added propargyl tosylate (1.0 g, 4.76 mmol), sodium bromide (500 mg, 4.86 mmol) and 1O mL of anhydrous acetonitrile. This mixture was stirred at 25°C. The mixture was clear initially and formed a slightly turbid mixture after 4 h. To this mixture was added, via Pasteur pipet, freshly distilled ethyl oxazoline (472 mg, 4.76 mmol). This mixture was stirred at 250C for 18 h giving a white mixture or suspension with no observable NaBr remaining in the mixture. To this mixture was added ethyl 1-piperazine carboxylate (800 mg, 5.05 mmol). This mixture was stirred for 4 h at 25°C and found to show no reaction as determined by TLC (MeOH). This mixture was heated at 55°C for 18 h under N2. A TLC (MeOH) of this mixture indicated some product at Rf 0.85 had formed along with the complete disappearance of the piperazine reagent.A MALDI -TOF mass spectrum indicated the complete disappearance of the peak at 136 amu for the N-propargyl-2-ethyl-2-oxazolinium cation and the appearance of a new peak at 296 amu for the desired product.

Reference： [1]Current Patent Assignee: STARPHARMA HOLDINGS LIMITED - WO2008/13618, 2008, A1 Location in patent: Page/Page column 14-15

23
[ 10431-98-8 ]
[ 6165-76-0 ]
[ 1004550-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: propargyl p-toluenesulfonate With sodium iodide In acetonitrile at 25℃; for 3h; Stage #2: 2-ethyl-4,5-dihydrooxazole In acetonitrile at 25℃; for 6h;	4; 5 Example 4: N-Propargyl-2-Ethyl-2-Oxazolinium Iodide from Propargyl Tosylate and Sodium Iodide; To a 25-mL round bottom flask containing a stir bar and flame - dried under N2 was added propargyl tosylate (1.0 g, 4.76 mmol), sodium iodide (830 rag, 5 mmol) and 10 mL of anhydrous acetonitrile. This mixture was stirred at 25°C for 3 h. The mixture was clear initially and formed a slightly turbid mixture after 3 h. To this mixture was added, via Pasteur pipet, freshly distilled ethyl oxazoline (475 mg, 4.79 mmol). This mixture was stirred at 25°C for 6 h giving a white mixture or suspension with no observable NaI remaining in the mixture.A MALDI - TOF mass spectrum of this mixture showed a peak at 136 amu for the desired N-propargyl-2-ethyl-2-oxazolinium cation.The following reaction scheme illustrates this process.4 hours, 25° C 1 B -24 hoursC15H25N3O3 Exact Mass: 295.19MoI. Wt: 295.38 C, 60.99; H, 8.53; N, 14.23; O, 16.25; Example S: Reaction of N-Propargyl-2-Ethyl-2-Oxazolinium Iodide with Ethyl 1- Piperazine Carboxylate; To a 25-mL round bottom flask containing a stir bar and flame - dried under N2 was added propargyl tosylate (1.0 g, 4.76 mmol), sodium iodide (830 mg, 5 mmol) and 10 mL of anhydrous acetonitrile. This mixture was stirred at 250C for 3 h. The mixture was clear initially and formed a slightly turbid mixture after 3 h. To this mixture was added, via Pasteur pipet, freshly distilled ethyl oxazoline (475 mg, 4.79 mmol). This mixture was stirred at 25°C for 6 h giving a white mixture or suspension with no observable NaI remaining in the mixture. To this mixture was added ethyl 1-piperazine carboxylate (800 mg, S.OS mmol). This mixture was stirred for 4 h at 25°C and found to show no reaction as determined by TLC (MeOH). This mixture was heated at 55°C for 18 h under N2. A TLC (MeOH) of this mixture indicated some product at Rf 0.85 had formed along with the complete disappearance of the piperazine reagent.A MALDI - TOF mass spectrum indicated the complete disappearance of the peak at 136 amu for the N-propargyl-2-ethyl-2-oxazolinium cation and the appearance of a new peak at 296 amu for the desired product. The volatiles of the reaction mixture were removed on a rotary evaporator. The resulting mixture was mixed with IS mL of MeOH and sodium carbonate (500 mg, 4.7 mmol) and purified through a plug of silica gel in MeOH to give 1.3 g (89% yield) of a light brown liquid. Its spectra are as follows:13C NMR (125 MHz, CDCl3) δ 10.12, 14.87, 26.47, 38.99, 43.70, 51.72, 52.81, 61.59, 73.75, 78.52, 155.81, 175.05.

Reference： [1]Current Patent Assignee: STARPHARMA HOLDINGS LIMITED - WO2008/13618, 2008, A1 Location in patent: Page/Page column 16-17

24
[ 35386-24-4 ]
[ 6165-76-0 ]
[ 21057-44-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; sodium iodide In acetone Reflux;	5.4. General procedure for preparation of alkynes 10a-d General procedure: An appropriate arylpiperazines (1.0 equiv), alkynyl tosylate (1.0 equiv), K2CO3 (2.0 equiv) and sodium iodide (cat.) were dissolved in acetone. The resulting mixture was refluxed overnight. The solvent was removed, and the crude material was dissolved in CH2Cl2 and water. After filtration, the solvent was removed and the residue was subjected to chromatography to give corresponding alkynes 10a-d.

Reference： [1]Location in patent: experimental part Ye, Na; Wu, Qianqian; Zhu, Liyuan; Zheng, Longtai; Gao, Bo; Zhen, Xuechu; Zhang, Ao [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 1999 - 2008]

25
[ 6165-76-0 ]
[ 68922-87-2 ]
[ 491862-29-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetra-(n-butyl)ammonium iodide In toluene at 80℃; for 2h; Inert atmosphere;

Reference： [1]Chiou, Wen-Hua; Lin, Yi-Huei; Chen, Guei-Tang; Gao, Yu-Kai; Tseng, Yu-Che; Kao, Chien-Lun; Tsai, Jui-Chi [Chemical Communications, 2011, vol. 47, # 12, p. 3562 - 3564]

26
[ 112-60-7 ]
[ 6165-76-0 ]
[ 87450-10-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium In tetrahydrofuran at 0℃;

Reference： [1]Location in patent: scheme or table Yin, Yanzhen; Huang, Xin; Lv, Chunyan; Wang, Liang; Yu, Shuangjiang; Luo, Quan; Xu, Jiayun; Liu, Junqiu [Macromolecular Bioscience, 2010, vol. 10, # 12, p. 1505 - 1516]

27
[ 6165-76-0 ]
[ 1338831-41-6 ]
[ 1338831-39-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: C₁₉H₁₈N₆O₃S With sodium azide In N,N-dimethyl-formamide at 80℃; Inert atmosphere; Stage #2: propargyl p-toluenesulfonate With copper(l) iodide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	General procedure: Synthesisofbis-andtris-1,2,3-triazoles General procedure: In a 50 mL two-neck flask under a nitrogen atmosphere, the starting material (0.5 mmol) was added with sodium azide (1.1 equiv, 0.55 mmol) dissolved in DMF. The mixture was stirred until the starting material was consumed, followed by TLC. After the conversion of the starting material, acetylene (1.2 equiv, 0.6 mmol) and the copper catalyst (1.0 equiv, 0.5 mmol) were added under vigorous stirring. At the end of reaction, the aqueous phase was washed with ethyl acetate, the organic phase was dried with MgSO4, filtered and the solvent was evaporated under vacuum.

Reference： [1]Location in patent: experimental part Stefani, Hélio A.; Canduzini, Hugo A.; Manarin, Flávia [Tetrahedron Letters, 2011, vol. 52, # 46, p. 6086 - 6090]

28
[ 88-04-0 ]
[ 6165-76-0 ]
[ 1248132-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	General procedure for the production of ethers 16a - 16c, 17a - 17c: General Procedure: To a solution of one of the phenols 3 - 5 (1 eq) and tosyl ester (1.2 eq) dissolved in dry DMF was added potassium carbonate (2.5 eq). The mixture was stirred at room temperature for either 20 hours (compounds C to E) or two days (F to H), at which point the starting material was no longer visible byTLC. The solvent was then removed under reduced pressure and the crude mixture was purified by flash chromatography (hexanes/ethyl acetate, 1/9), to afford the phenol-alkynes 16a - 16c, 17a - 17c as white solids (51 - 96%, 69 - 92%).

Reference： [1]Findlay, Brandon; Zhanel, George G.; Schweizer, Frank [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1499 - 1503]

29
[ 6165-76-0 ]
[ 67651-56-3 ]
[ 1357190-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	General procedure for the production of ethers 16a - 16c, 17a - 17c: General Procedure: To a solution of one of the phenols 3 - 5 (1 eq) and tosyl ester (1.2 eq) dissolved in dry DMF was added potassium carbonate (2.5 eq). The mixture was stirred at room temperature for either 20 hours (compounds C to E) or two days (F to H), at which point the starting material was no longer visible byTLC. The solvent was then removed under reduced pressure and the crude mixture was purified by flash chromatography (hexanes/ethyl acetate, 1/9), to afford the phenol-alkynes 16a - 16c, 17a - 17c as white solids (51 - 96%, 69 - 92%).

Reference： [1]Findlay, Brandon; Zhanel, George G.; Schweizer, Frank [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1499 - 1503]

30
[ 6165-76-0 ]
[ 37693-01-9 ]
[ 1357190-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	General procedure for the production of ethers 16a - 16c, 17a - 17c: General Procedure: To a solution of one of the phenols 3 - 5 (1 eq) and tosyl ester (1.2 eq) dissolved in dry DMF was added potassium carbonate (2.5 eq). The mixture was stirred at room temperature for either 20 hours (compounds C to E) or two days (F to H), at which point the starting material was no longer visible byTLC. The solvent was then removed under reduced pressure and the crude mixture was purified by flash chromatography (hexanes/ethyl acetate, 1/9), to afford the phenol-alkynes 16a - 16c, 17a - 17c as white solids (51 - 96%, 69 - 92%).

Reference： [1]Findlay, Brandon; Zhanel, George G.; Schweizer, Frank [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1499 - 1503]

31
[ 6165-76-0 ]
[ 1068-90-2 ]
[ 61172-60-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 2-acetylaminomalonic acid diethyl ester With potassium <i>tert</i>-butylate In 1,4-dioxane at 20 - 50℃; for 4h; Inert atmosphere; Stage #2: propargyl p-toluenesulfonate In 1,4-dioxane at 50℃; Inert atmosphere; Reflux;	Synthesis of diethyl α-propargyl-α-acetamidomalonate (5) To a solution of 105 g (0.483 mol) of diethyl 2-acetamidomalonate (4) in 1.35 L of dioxane was added a slurry of 61 g (0.54 mol) of potassium tert-butoxide in 550 mL of dioxane dropwise via cannula over 2 h while stirring with a mechanical stirrer at room temperature. The resulting suspension was heated to 50 °C and stirred for another 2 h. A solution of propargyl tosylate (83 mL, 0.49 mol) in 150 mL of dioxane was added dropwise at 50 °C over 1 h and the resulting mixture was brought to reflux overnight. The reaction mixture was cooled to room temperature and filtered to remove the solid. The filtrate was concentrated on rotavap and the crude product was dissolved in 1 L of dichloromethane. The organic layer was washed with water (2 × 500 mL), decolorized with activated charcoal and dried over anhydrous Na2SO4. The desired product diethyl α-propargyl-α-acetamidomalonate (5) was obtained as a light yellow solid [31] in 99.0% yield (122 g) by solvent evaporation and drying under vacuum.

Reference： [1]Zhang, Quanxuan; Ren, Hong; Baker, Gregory L. [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1365 - 1371]

32
[ 6165-76-0 ]
[ 90098-04-7 ]
3-prop-2-ynyl 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.7 g	In N,N-dimethyl-formamide; at 20 - 80℃;	General procedure: To a compound of Chemical Formula II are sequentially added DMF (dimethylformamide, 8?10 volumes of the compound of Chemical Formula II), a sulfonate compound (1?1.5 equivalents), and an inorganic salt (1?2 equivalents), and the resulting mixture is allowed to react at 20~80C for 1?24 hrs. After completion of the reaction, the product is obtained by filtration, followed by removing DMF in a vacuum. The residue is subjected to column chromatography using methylene chloride: methanol (9:1, v/v) to afford the compound of Chemical Formula 1 as a solid. If necessary, recrystallization is carried out According to Experiment Prototocol D, 1.0 g(2.69 mmol) of <strong>[90098-04-7]rebamipide</strong> and 0.84 g(1.5 eq, 4.03 mmol) of propargyl tosylate were reacted to afford the title compound as a white solid (0.7 g). 1H NMR (700MHz, DMSO-d6):delta 11.66(s, 1H), 9.07(d, 1H), 7.84-7.80(m, 3H), 7.57(s, 1H), 7.55(s, 1H), 7.51(t, 1H), 7.31(d, 1H), 7.23(t, 1H), 6.45(s, 1H), 4.81-4.76(m, 2H), 3.50-43(m, 1H), 3.32-3.26(m, 3H)
0.7 g	In N,N-dimethyl-formamide; at 20 - 80℃;	General procedure: Example 26 Preparation of 3-Prop-2-ynyl 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionate According to Experiment Prototocol D, 1.0 g (2.69 mmol) of <strong>[90098-04-7]rebamipide</strong> and 0.84 g (1.5 eq, 4.03 mmol) of propargyl tosylate were reacted to afford the title compound as a white solid (0.7 g). 1H NMR (700 MHz, DMSO-d6): delta 11.66 (s, 1H), 9.07 (d, 1H), 7.84-7.80 (m, 3H), 7.57 (s, 1H), 7.55 (s, 1H), 7.51 (t, 1H), 7.31 (d, 1H), 7.23 (t, 1H), 6.45 (s, 1H), 4.81-4.76 (m, 2H), 3.50-43 (m, 1H), 3.32-3.26 (m, 3H); To a compound of Chemical Formula II are sequentially added DMF (dimethylformamide, 810 volumes of the compound of Chemical Formula II), a sulfonate compound (11.5 equivalents), and an inorganic salt (12 equivalents), and the resulting mixture is allowed to react at 2080 C. for 124 hrs. After completion of the reaction, the product is obtained by filtration, followed by removing DMF in a vacuum. The residue is subjected to column chromatography using methylene chloride:methanol (9:1, v/v) to afford the compound of Chemical Formula 1 as a solid. If necessary, recrystallization is carried out.
0.7 g	With inorganic salt; In N,N-dimethyl-formamide; at 20 - 80℃;	General procedure: To a compound of Chemical Formula II are sequentially added DMF(dimethylformamide, 810 volumes of thecompoundof Chemical Formula II), a sulfonate compound (11.5 equivalents), and aninorganic salt (12equivalents),and the resulting mixture is allowed to react at 2080 C. for 124 hrs. Aftercompletion of thereaction,the product is obtained by filtration, followed by removing DMF in a vacuum.The residue is subjected tocolumnchromatography using methylene chloride:methanol (9:1, v/v) to afford thecompound of ChemicalFormula 1 as a solid. If necessary, recrystallization iscarried out. According to Experiment Prototocol D, 1.0 g (2.69 mmol) of <strong>[90098-04-7]rebamipide</strong> and 0.84 g (1.5 eq, 4.03 mmol) ofpropargyl tosylate were reacted to afford the title compound as a white solid (0.7 g).

Reference： [1]Patent: EP2865669,2015,A1 .Location in patent: Paragraph 0040; 0041; 0106; 0107
[2]Patent: US2015/141409,2015,A1 .Location in patent: Paragraph 0233; 0324; 0325; 0326
[3]Patent: KR2015/3106,2015,A .Location in patent: Paragraph 0259; 0377-0379

33
[ 256-96-2 ]
[ 6165-76-0 ]
[ 152700-49-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;	General Procedure for the Synthesis of 5-(Prop-2-ynyl)-5H-dibenzo[b,f]azepine (6) In a typical reaction, iminostilbene (1.5 mmol) was dissolved in DMF (3 mL) and potassium carbonate (3.0 mmol) was added at 0 °C. Then propargyl bromide (4.5 mmol) was slowly added and reaction mixture was refluxed for 15 h at 90 °C. Completion of the reaction was judged by TLC analysis. After completion, crude mixture was adsorbed on silicagel and purified by column chromatography using n-hexanes and ethyl acetate (9.5 : 0.5) as an eluent to afford desired product in 77% yield. IR (KBr, cm-1): 3271 (CC-H), 3050, 3021, 2926, 2842, 2119 (CC), 1631, 1591, 1569, 1483, 1454,1117, 763; 1H NMR (300 MHz, CDCl3): 7.23 (4H, m, ArH),7.02 (4H, m, ArH), 6.71 (2H, s, 2C=CH), 4.44 (2H, d,J = 2.4 Hz, CH2), 2.22 (1H, t, J = 2.4 Hz, CC-H); MS (EI)m/z (rel. abund. %): 231 (M+, 39), 192 (100), 165 (39).

Reference： [1]Khan, Maria Aqeel; Saleem, Aliyan; Ghouri, Nida; Hameed, Abdul; Iqbal Choudhary; Basha, Fatima Z. [Letters in drug design and discovery, 2015, vol. 12, # 7, p. 597 - 606]

34
[ 6165-76-0 ]
[ 1246999-39-2 ]
C₂₆H₂₃NO₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	2.7 (7) Synthesis of Compound A51 A41 (0.7 mmol, 287 mg) was added to a one-necked flask,Then weighed 9.7mg CuI and 20.3mg Pd (PPh3) 4 added to the reaction flask,Vacuum, nitrogen protection, wrapped in aluminum foil, add 2.3ml DMF, stirred to dissolve, add 0.2ml TEA,Weigh propargyl p-toluenesulfonate (357mg, 1.7mmol) dissolved in 2.7ml of DMF was added to the above reaction flask, stirred at room temperature, the reaction overnight, after the reaction was completed, the solvent was evaporated to dryness under reduced pressure,Direct column chromatography isolated 284mg, 83% yield.

Reference： [1]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN104725453, 2017, B Location in patent: Paragraph 0079; 0086

35
[ 6165-76-0 ]
[ 93298-14-7 ]
C₂₄H₂₁NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	2.2 (2) Synthesis of Compound A11 Compound 2 (0 .7 mmol, 247 mg) was added to a one-necked flask,Then weighed 9.7mg CuI and 20.3mg Pd (PPh3) 4 added to the reaction flask, Vacuum, nitrogen protection, aluminum foil package, and added 2.3ml DMF, stirred to dissolve, add 0.2 ml TEA, weigh propargyl p-toluenesulfonate (357mg, 1.7mmol) was dissolved with 2.7ml of DMF was added to the above reaction flask, Stirred at room temperature, the reaction overnight, After the reaction was over, the solvent was evaporated to dryness under reduced pressure, and 249 mg of the product was directly isolated by column chromatography with a yield of 82%.

Reference： [1]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN104725453, 2017, B Location in patent: Paragraph 0079; 0081

36
[ 107-19-7 ]
[ 824-79-3 ]
[ 6165-76-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With [bis(acetoxy)iodo]benzene at 20℃; for 0.25h;	a) General procedure for the formation of sulfonate 4 General procedure: Iodobenzene diacetate (DIB, 0.24 mmol, 1.2 equiv) was added at room temperature to avigorously stirred solution of dichloromethane (0.5 mL), alcohol (0.5 mL), sulfinate (0.2mmol, 1 equiv) and acetic acid (0.01 to 0.05 mL) or TBAC (55.5 mg, 0.2 mmol, 2 equiv) tosolve the sulfonate salt. The mixture was then stirred for 15 min (followed by TLC with amixture of acetic acid/ethyl acetate/hexane) and then filtered on silica with ethyl acetate.The residue was purified by silica gel chromatography with a mixture of ethylacetate/hexane to give sulfonate product 4, 6 and 8.

Reference： [1]Deruer, Elsa; Hamel, Vincent; Blais, Samuel; Canesi, Sylvain [Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1203 - 1207]

37
[ 864070-37-1 ]
[ 6165-76-0 ]
(3R,4R,5S,6R)-2-(3-(4-prop-2-ynyloxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.4%	Stage #1: (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol With caesium carbonate In N,N-dimethyl-formamide at 55℃; for 0.216667h; Stage #2: propargyl p-toluenesulfonate In N,N-dimethyl-formamide at 60℃; for 15h;	11 Synthesis of (3R,4R,5S,6R)-2-(3-(4-prop-2-ynyloxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (13e) 1.7 g (4.5 mmol) of 10 and 2.1 g (6.8 mmol) of cesium carbonate were added to 9 mL of N,N-dimethylformamide under an oil bath of 55 ° C for 13 min.Add 1.24g (5.9mmol) to the oil bath at 60 ° CPropyl p-toluenesulfonate 1 and stirred for 15 h,Add saturated brine, extract with ethyl acetate, and dry over anhydrous sodium sulfate.Filter and distill off the solvent under reduced pressure.The residue was subjected to silica gel column chromatography (dichloromethane:methanol = 20:1) to yield 1.89 g of colorless viscous solid 13e, yield 76.4%.

Reference： [1]Current Patent Assignee: TIANJIN TASLY GROUP COMPANY., LTD. - CN108285439, 2018, A Location in patent: Paragraph 0038; 0121-0123

38
[ 6165-76-0 ]
[ 622-34-4 ]
[ 93439-98-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 16h; Sealed tube; Inert atmosphere;

Reference： [1]Ayres, James N.; Williams, Matthew T.J.; Tizzard, Graham J.; Coles, Simon J.; Ling, Kenneth B.; Morrill, Louis C. [Organic Letters, 2018, vol. 20, # 17, p. 5282 - 5285]

39
[ 6165-76-0 ]
[ 696-23-1 ]
[ 22927-54-4 ]

Reference： [1]Applied Organometallic Chemistry,2019,vol. 33

40
[ 6165-76-0 ]
1-phenylhex-2-yn-1-one-O-methyloxime ether [ No CAS ]
[ 109-89-7 ]
C₁₉H₂₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
88%	With azacyclic carbene palladium at 70℃; for 12h;	16 Example 16 In a 15mL round-bottomed flask, add 0.003mol of azacyclic carbene palladium, 0.10mmol of 1-phenyl-2-hexyn-1-one O-methyl oxime ether, 0.15mmol of propynyl p-toluenesulfonate, 0.30 mmol of ethylenediamine, 1 mL of [Bmim]Cl, stirred and reacted at 70 °C for 12 hours, stopped heating and stirring, cooled to room temperature, and distilled under reduced pressure to obtain the crude product, The target product is obtained by separation and purification by column chromatography. The column chromatography eluent used is a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 100:1, and the yield is 88%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0106-0115

41
[ 6165-76-0 ]
1-phenyl-3-cyclopropyl-2-propyn-1-one-O-methyl oxime [ No CAS ]
[ 109-89-7 ]
C₁₉H₂₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
80%	With azacyclic carbene palladium at 70℃; for 12h;	17 Example 17 In a 15 mL round-bottomed flask, add 0.003 mol of azacyclic carbene palladium, 0.10 mmol of 1-phenyl-3-cyclopropyl-2-propyn-1-one O-methyl oxime ether, 0.15 mmol of propynyl p-toluenesulfonate, 0.30 mmol of ethylenediamine, 1 mL of [Bmim]Cl, after stirring the reaction at 70°C for 12 hours, Heating and stirring were stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether: ethyl acetate with a volume ratio of 100:1. mixed solvent, yield 80%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0116-0125

42
[ 6165-76-0 ]
1-phenyl-3-(2-thienyl)-2-propyn-1-one-O-methyl oxime [ No CAS ]
[ 109-89-7 ]
C₂₀H₂₀N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
76%	With azacyclocarbene palladium at 70℃; for 12h;	18 Example 18 In a 15 mL round-bottomed flask, add 0.003 mol of azacyclic carbene palladium, 0.10 mmol of 1-phenyl-3-(2-thienyl)-2-propyn-1-one O-methyl oxime ether, 0.15 mmol of propynyl p-toluenesulfonate, 0.30 mmol of ethylenediamine, 1 mL of [Bmim]Cl, after stirring the reaction at 70°C for 12 hours, The heating and stirring were stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether with a volume ratio of 50:1: ethyl acetate mixed solvent, yield 76%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0126-0135

43
[ 6165-76-0 ]
3-(4-(tert-butyl)phenyl)-1-phenylprop-2-yn-1-one O-methyloxime [ No CAS ]
[ 109-89-7 ]
C₂₆H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
82%	With azacyclocarbene palladium at 70℃; for 12h;	14 Example 14 In a 15mL round-bottomed flask, add 0.003mol azacyclocarbene palladium, 0.10mmol 1-phenyl-3-(4-tert-butylphenyl)-2-propyn-1-one O-methyl oxime ether, 0.15mmol propynyl p-toluenesulfonate, 0.30mmol ethylenediamine, 1mL [Bmim]Cl, stir at 70°C for 12 hours, stop heating and stirring, Cooled to room temperature, the crude product was obtained by distillation under reduced pressure, The target product is obtained by separation and purification by column chromatography. The column chromatography eluent used is a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 50:1, and the yield is 82%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0086-0095

44
[ 6165-76-0 ]
[ 109-89-7 ]
5-phenyl-2,2-dimethylpent-4-yn-3-one-O-methyloxime ether [ No CAS ]
C₂₀H₂₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
86%	With azacyclocarbene palladium at 70℃; for 12h;	19 Example 19 In a 15 mL round-bottomed flask, add 0.003 mol of azacyclocarbene palladium, 0.10 mmol of 1-phenyl-4,4-dimethyl-1-pentyn-3-one O-methyl oxime ether, 0.15 mmol of propynyl p-toluenesulfonate, 0.30 mmol of ethylenediamine, 1 mL of [Bmim]Cl, after stirring the reaction at 70°C for 12 hours, Heating and stirring were stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether: ethyl acetate with a volume ratio of 100:1. mixed solvent, yield 86%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0136-0145

45
[ 6165-76-0 ]
1-(3-thienyl)-3-phenyl-2-propyn-1-one-O-methyl oxime [ No CAS ]
[ 109-89-7 ]
C₂₀H₂₀N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
65%	With azacyclic carbene palladium at 70℃; for 18h;	20 Example 20 In a 15 mL round-bottomed flask, add 0.003 mol of azacyclic carbene palladium, 0.10 mmol of 1-(3-thienyl)-3-phenyl-2-propyn-1-one O-methyl oxime ether, 0.15 mmol of propynyl p-toluenesulfonate, 0.30 mmol of ethylenediamine, 1 mL of [Bmim]Cl, after stirring the reaction at 70°C for 18 hours, Heating and stirring were stopped, cooled to room temperature, and the crude product was obtained by distillation under reduced pressure, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether with a volume ratio of 50:1: ethyl acetate mixed solvent, yield 65%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0146-0155

46
[ 6165-76-0 ]
1-phenyl-3-(4-ethoxyphenyl)-2-propyn-1-one-O-methyl oxime [ No CAS ]
[ 109-89-7 ]
C₂₄H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
76%	With azacyclic carbene palladium at 70℃; for 12h;	15 Example 15 In a 15 mL round-bottomed flask, add 0.003 mol of azacyclic carbene palladium, 0.10 mmol of 1-phenyl-3-(4-ethoxyphenyl)-2-propyn-1-one O-methyl oxime ether, 0.15mmol propynyl p-toluenesulfonate, 0.30mmol ethylenediamine, 1mL [Bmim]Cl, stir at 70°C for 12 hours, stop heating and stirring, Cool to room temperature, distill under reduced pressure to obtain the crude product, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 20:1. The yield is 76%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0096-0105

47
[ 6165-76-0 ]
1-phenyl-3-(4-ethylphenyl)-2-propyn-1-one-O-methyl oxime [ No CAS ]
[ 109-89-7 ]
C₂₄H₂₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With NHC-Pd(II)-Im at 70℃; for 12h; Ionic liquid; Green chemistry;
81%	With azacyclic carbene palladium at 70℃; for 12h;	13 Example 13 In a 15 mL round-bottomed flask, add 0.003 mol of azacyclic carbene palladium, 0.10 mmol of 1-phenyl-3-(4-ethylphenyl)-2-propyn-1-one O-methyl oxime ether, 0.15mmol propynyl p-toluenesulfonate, 0.30mmol ethylenediamine, 1mL [Bmim]Cl, stir at 70°C for 12 hours, stop heating and stirring, Cooled to room temperature, distilled under reduced pressure to obtain the crude product, and then separated and purified by column chromatography to obtain the target product. The column chromatography eluent used was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 50:1, and the yield was 81%.

Reference： [1]Li, Jianxiao; Huang, Ruikang; Li, Can; Lin, Shao; Wu, Wanqing; Jiang, Huanfeng [Chemistry - An Asian Journal, 2019, vol. 14, # 13, p. 2309 - 2315]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109438380, 2022, B Location in patent: Paragraph 0076-0085

48
[ 2157-52-0 ]
[ 6165-76-0 ]
[ 1370596-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; dimethyl sulfoxide; at 20℃; for 2h;	General procedure: In a round-bottomed flask (100mL), propargyl tosylate (2.73g, 0.013mol) was added portionwise to a soln. of an appropriate oxime (0.01mol), KOH (0.56g, 0.01mol), and 2mL of H2O in DMSO (18mL). The mixture was stirred for 2h at r.t. (TLC control). Then, the crude product was dissolved in CHCl3 (150mL) and washed with H2O (3×200mL). The organic layer was dried (Na2SO4, 10g) and concentrated to afford the crude product, which was purified by column chromatography (SiO2, n-hexane/EtOAc 10:1).

Reference： [1]Journal of Molecular Liquids,2020,vol. 299

49
[ 6165-76-0 ]
C₂₂H₂₁NO₂ [ No CAS ]
C₂₅H₂₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 2h;	2.6 Synthesis of O-propargyl oxime ethers 8 and 12 General procedure: In a round-bottomed flask (100mL), propargyl tosylate (2.73g, 0.013mol) was added portionwise to a soln. of an appropriate oxime (0.01mol), KOH (0.56g, 0.01mol), and 2mL of H2O in DMSO (18mL). The mixture was stirred for 2h at r.t. (TLC control). Then, the crude product was dissolved in CHCl3 (150mL) and washed with H2O (3×200mL). The organic layer was dried (Na2SO4, 10g) and concentrated to afford the crude product, which was purified by column chromatography (SiO2, n-hexane/EtOAc 10:1).

Reference： [1]Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Saremi, Hossein; Mohammadtaghi-Nezhad, Javad [Journal of Molecular Liquids, 2020, vol. 299]

50
[ 574-66-3 ]
[ 6165-76-0 ]
benzophenone O-(prop-2-yn-1yl)oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 2h;	2.6 Synthesis of O-propargyl oxime ethers 8 and 12 General procedure: In a round-bottomed flask (100mL), propargyl tosylate (2.73g, 0.013mol) was added portionwise to a soln. of an appropriate oxime (0.01mol), KOH (0.56g, 0.01mol), and 2mL of H2O in DMSO (18mL). The mixture was stirred for 2h at r.t. (TLC control). Then, the crude product was dissolved in CHCl3 (150mL) and washed with H2O (3×200mL). The organic layer was dried (Na2SO4, 10g) and concentrated to afford the crude product, which was purified by column chromatography (SiO2, n-hexane/EtOAc 10:1).

Reference： [1]Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Saremi, Hossein; Mohammadtaghi-Nezhad, Javad [Journal of Molecular Liquids, 2020, vol. 299]

51
[ 10341-75-0 ]
[ 6165-76-0 ]
(E)-acetophenone O-propargyloxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 2h;	2.6 Synthesis of O-propargyl oxime ethers 8 and 12 General procedure: In a round-bottomed flask (100mL), propargyl tosylate (2.73g, 0.013mol) was added portionwise to a soln. of an appropriate oxime (0.01mol), KOH (0.56g, 0.01mol), and 2mL of H2O in DMSO (18mL). The mixture was stirred for 2h at r.t. (TLC control). Then, the crude product was dissolved in CHCl3 (150mL) and washed with H2O (3×200mL). The organic layer was dried (Na2SO4, 10g) and concentrated to afford the crude product, which was purified by column chromatography (SiO2, n-hexane/EtOAc 10:1).

Reference： [1]Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Saremi, Hossein; Mohammadtaghi-Nezhad, Javad [Journal of Molecular Liquids, 2020, vol. 299]

52
[ 39807-19-7 ]
[ 6165-76-0 ]
[ 39807-15-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In toluene for 4h; Reflux;	2-6 Example 2: 0.1molOxadiazonAdd 50mL of toluene,0.11mol of propargyl p-toluenesulfonate,Anhydrous potassium carbonate 0.12mol, stirred for 4h under reflux,Sampling HPLC analysis of oxadiazon content of 0.6%, filtration, washing with 10mL toluene, the filtrate was distilled off under reduced pressure,Add 20mL of ethanol to recrystallize, filter, dry,97% purity by HPLC analysis, 0.096 mol of propynoxazone,The yield was 96%.

Reference： [1]Current Patent Assignee: ANHUI UNIVERSITY - CN110776475, 2020, A Location in patent: Paragraph 0027-0036

53
1-(3-chloropyrazolo[1,5-a]-4,5,6,7-tetrahydropyridin-2-yl)-5-(N-methylamino)-1H-pyrazole-4-carbonitrile [ No CAS ]
[ 6165-76-0 ]
1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium carbonate In methanol at 10℃; for 15h;	7.7.1; 7.7.2 7.2) Pyraclonil Preparation Example 2 150ml of methanol, 1- (3chloro-pyrazolo [1,5-a] -4,5,6,7-tetrahydropyridin-2-yl) -5- (N-methylamine base ) -1H pyrazole -4-carbonitrile 0.05 mol, mix and stir 0.08mol of sodium carbonate, add propargyl p-toluenesulfonate dropwise at 10 0.055mol (dissolved in 30ml methanol), React for 15h, after the reaction is completed, concentrate in vacuo to 90ml Methanol. Add 350ml water, then freeze to -5 0% to crystallize and filter to obtain about 21g of wet product. Then add 105g butanone and 105g water, stir to heat up to 70%, keep it warm for 1h, freeze again to -5% to 0% for crystallization and filtration, 70%And dried in vacuo to give more of the following 5h pyraclonil, yielding about 94%.

Reference： [1]Current Patent Assignee: HUBEI XIANGHE PREC CHEMICAL - CN105001221, 2016, B Location in patent: Paragraph 0091-0095

54
[ 111-90-0 ]
[ 6165-76-0 ]
[ 89635-80-3 ]

Yield	Reaction Conditions	Operation in experiment
40%		To a suspension of pure NaH (2.40 g, 100 mmol) in anhyd DME (100 mL) was slowly added <strong>[111-90-0]2-(2-ethoxyethoxy)ethanol</strong> (13.42 g, 100 mmol) at r.t. After stirring for 30 min, the now clear solution was treated with 3-bromoprop-1-yne (11.9 g, 100 mmol) in PhMe (2 mL) over a period of 15 min (violent reaction) with vigorous stirring. The resulting blend was heated to reflux for 4 h, allowed to cool to r.t., and filtered. Addition of H2O (300 mL) was followed by extraction with CH2Cl2 (3 × 100 mL), and the organic layers were combined, washed with H2O (3 × 100 mL), and dried (MgSO4). Evaporation of the solvents under reduced pressure and vacuum distillation of the residual liquid gave 6a as a colorless liquid; yield: 12.9 g (75%); bp 47-48 C/0.1 Torr. Employment of prop-2-yn-1-yl 4-methylbenzenesulfonate in DME instead of 3-bromoprop-1-yne generated 6a in only 40% yield. IR (film): 3251, 2975, 2868, 2114, 1444, 1349, 1289, 1246, 1107, 1033, 948, 920, 844, 671 cm-1. 1H NMR (300 MHz, CDCl3): delta = 4.19 (d, J = 2.4 Hz, 2 H), 3.68 (AA'BB'm, 4 H), 3.64 (AA'm, 2 H), 3.58 (BB'm, 2 H), 3.51 (q, J = 7.0 Hz, 2 H), 2.40 (t, J = 2.4 Hz, 1 H), 1.19 (t, J = 7.0 Hz, 3 H). 13C NMR (100 MHz, CDCl3): delta = 79.3 (CH), 74.3 (Cquat), 70.4 (CH2), 70.1 (CH2), 69.5 (CH2), 68.8 (CH2), 66.3 (CH2), 58.0 (CH2), 14.8 (CH3). MS (EI, 70 eV): m/z (%) = 173 ([MH+], 55), 127 (10), 117 (10), 103 (20), 83 (40), 73 (100), 59 (70). HRMS (EI, 70 eV): m/z [MH+] calcd for C9H17O3: 173.1178; found: 173.1173.

Reference： [1]Synthesis,2020,vol. 52,p. 1287 - 1300

55
[ 6165-76-0 ]
[ 1684-40-8 ]
N-(prop-2-yn-1-yl)-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h;	Step 2: Moreover, 145mg (0.73mmol) of tetrahydroacridine hydrochloride were placed in a reaction flask and dissolved in 3mL of dry DMF, 140µL of tosylated propargyl alcohol (0.8mmol) were added and then 1.36mmol (76mg) of KOH. The reaction mixture was vigorously stirred for 3h, and then 5mL of H2O were added and partitioned with diethyl ether (5×10mL). The organic layers were combined, dried with anhydrous Na2SO4 and evaporated under reduced pressure. 86mg of impure tacrine derivative were recovered.

Reference： [1]Borioni, José L.; Cavallaro, Valeria; Murray, Ana P.; Peñéñory, Alicia B.; Puiatti, Marcelo; García, Manuela E. [Bioorganic Chemistry, 2021, vol. 111]

56
[ 6165-76-0 ]
[ 104-88-1 ]
[3-(4-chlorophenyl)isoxazol-5-yl]methyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sode de l'acide trichloroisocyanurique In water at 25℃; for 0.416667h; Sonication; Green chemistry;	General procedure for the one-pot synthesis of compounds (5a-j) General procedure: General procedure for the one-pot synthesis of compounds (5a-j): To solution of propargyl alcohol 2a (1 mmol) or propargylamine 2b (1 mmol) and K2CO3 (1 mmol) in H2O (10 mL) was added R1SO2Cl 1 (1.1 mmol) (R1=Me (1a); R1=Ph (1b); R1= p-CH3-C6H4 (1c)) dropwise. The reaction mixture was stirred for 2h (or sonicated for 10 min) at 25°C. Then the aromatic aldehyde 3a-f (1 mmol) and hydroxylamine hydrochloride 4 (1.2 mmol) and NaDCC (0.5 mmol) were added successively and the mixture was sonicated according to the time reported in Table 3 using the ultrasonic bath (47kHz). The completion of the reaction was monitored by TLC. The mixture was extracted with CH2Cl2 (20 mL x 2). The organic phase was washed with water (20 mL) and saturated brine solution (20 mL), dried over MgSO4 and concentrated in vacuum to give the crude products, which were purified by recrystallisation in EtOH to afford the pure adducts 5a-j

Reference： [1]Talha, Aicha; Tachallait, Hamza; Benhida, Rachid; Bougrin, Khalid [Tetrahedron Letters, 2021, vol. 81]

57
[ 6165-76-0 ]
N<SUP>6</SUP>-formyladenosine [ No CAS ]
[ 67005-97-4 ]

Yield	Reaction Conditions	Operation in experiment
24%	With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 30℃; for 0.25h;	3. Chemical labelling of f⁶A General procedure: Add f6A (29.5 mg, 0.1 mmol), electrophiles (0.3 mmol), potassium carbonate (21 mg, 0.15mmol), 18-crown-6 (40 mg, 0.15 mmol), DMF (2 mL) in a single-necked bottle in sequence ,stirring at 30 oC. TLC detects that the raw material has disappeared, and the product is separatedby thin layer chromatography (DCM/MeOH 6/1, 0.01% NH3•H2O).

Reference： [1]Xie, Li-Jun; Lin, Cui-Lian; Liu, Li; Cheng, Liang [Chinese Chemical Letters, 2022, vol. 33, # 3, p. 1563 - 1566]

58
[ 6165-76-0 ]
[ 54840-15-2 ]
[ 54840-30-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide In methanol; lithium hydroxide monohydrate at 100℃; for 12h; Inert atmosphere;	2.4. Synthesis of N-boc-4-aminophenyl-1-propargyl ether (2) In a 50-mL three-necked round-bottom flask equipped with a magnetic stirrer, condenser, dropping funnel and a nitrogen inlet/outlet 1 (6.27 g, 0.03 mol) and NaOH (1.38 g, 0.035 mol) were added in a mixture of 8 mL of deionized water and 17 mL of methanol. The mixture was heated to 100 °C under N2 atmosphere and then P-Ts (6.3 g, 0.03 mol) was added dropwise to the reaction mixture during 20 min. After the addition of P-Ts was finished, the reaction was carried out for 12 h. At the end of the reaction, the mixture was cooled to room temperature and the product was extracted with ethyl acetate. Then product was washed with deionized water and dried over a sodium sulfate. The solvent was evaporated to give a crude product. Purification by column chromatography on silica gel (eluent dichloromethane) yielded pure compound. Yield: 82%, m. p. = 82 °C. Anal. Calcd for C14H17NO3: C, 68.00; H, 6.93; N, 5.66; found: C, 68.02; H, 7.08; N, 5.65. FT-IR (CsI, cm -1): 3362 (N-H), 3285 (≡C-H), 2980 and 2870 (asymmetric and symmetric C-H stretching of CH3, respectively), 2134 (C≡C), 1698 (C=O), 1525 (C-C aromatic), 1257 (C-O-C). 1H NMR (300 MHz, CDCl3) δ: 7.27 (d, 2H, J = 9.3 Hz, Ar-H), 6.93-6.86 (m, 2H, Ar-H), 6.41 (br. s, 1H, N-H), 4.64 (d, 2H, J = 9.3 Hz, -CH2-), 2.49 (t, 1H, J = 2.4 Hz, ≡C-H), 1.49 (s, 9H -CH3). 13C NMR (75 MHz, CDCl3) δ: 153.50, 153.08, 132.34, 120.39, 115.45, 80.34, 78.64, 75.46, 56.21, 28.36.

Reference： [1]Belousov, Sergey I.; Buzin, Alexander I.; Cherkaev, Georgij V.; Dmitryakov, Petr V.; Drozdov, Fedor V.; Kechekyan, Alexander S.; Kolesnikov, Timofey I.; Kuznetsov, Alexander A.; Orlova, Alexandra M. [Polymer, 2022, vol. 254]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	6165-76-0	MDL No. :	MFCD01462194
Formula :	C₁₀H₁₀O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LMBVCSFXFFROTA-UHFFFAOYSA-N
M.W :	210.25	Pubchem ID :	22547
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.36
TPSA :	51.75 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	1.68
Log Po/w (WLOGP) :	2.49
Log Po/w (MLOGP) :	2.32
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	2.08

[ CAS No. 6165-76-0 ] {[proInfo.proName]}

Quality Control of [ 6165-76-0 ]

Related Doc. of [ 6165-76-0 ]

Product Details of [ 6165-76-0 ]

Calculated chemistry of [ 6165-76-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6165-76-0 ]

Application In Synthesis of [ 6165-76-0 ]

[ 6165-76-0 ] Synthesis Path-Upstream 1~1

[ 6165-76-0 ] Synthesis Path-Downstream 1~58

Related Functional Groups of
[ 6165-76-0 ]

Aryls

Alkynes

Sulfonates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.32
Solubility :	1.0 mg/ml ; 0.00477 mol/l
Class :	Soluble
Log S (Ali) :	-2.38
Solubility :	0.874 mg/ml ; 0.00416 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.94
Solubility :	0.239 mg/ml ; 0.00114 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.56

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:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 6165-76-0 ] {[proInfo.proName]}

Quality Control of [ 6165-76-0 ]

Related Doc. of [ 6165-76-0 ]

Product Details of [ 6165-76-0 ]

Calculated chemistry of [ 6165-76-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6165-76-0 ]

Application In Synthesis of [ 6165-76-0 ]

[ 6165-76-0 ] Synthesis Path-Upstream 1~1

[ 6165-76-0 ] Synthesis Path-Downstream 1~58

Related Functional Groups of [ 6165-76-0 ]

Aryls

Alkynes

Sulfonates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6165-76-0 ]