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Quality Control of [ 143321-89-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 143321-89-5 ]

CAS No. :	143321-89-5	MDL No. :	MFCD00547381
Formula :	C₈H₅F₃INO	Boiling Point :	-
Linear Structure Formula :	C₈H₅F₃ION	InChI Key :	-
M.W :	315.03	Pubchem ID :	-
Synonyms :

Safety of [ 143321-89-5 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 143321-89-5 ]

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

Upstream synthesis route of [ 143321-89-5 ]
Downstream synthetic route of [ 143321-89-5 ]

[ 143321-89-5 ] Synthesis Path-Upstream 1~2

1
[ 143321-89-5 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 6, p. 1035 - 1038

2
[ 143321-89-5 ]
[ 766-97-2 ]
[ 55577-25-8 ]
[ 124643-45-4 ]

Reference： [1] Tetrahedron, 2001, vol. 57, # 38, p. 8017 - 8028

[ 143321-89-5 ] Synthesis Path-Downstream 1~25

1
[ 615-43-0 ]
[ 407-25-0 ]
[ 143321-89-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In tetrahydrofuran at -15 - 25℃; for 13h;	2-(3-Hydroxypropyl)indole (S7)³² To a solution of 2-iodoaniline (0.3 g, 1.37 mmol) and Et3N (0.22 mL, 1.64 mmol) in THF (3.4 mL) at -15°C was added dropwise a THF solution (1.0 mL) of (CF3CO)2O (0.2 mL, 1.51 mmol). The mixture was stirred at -15°C for 1 h, allowed to warm up to room temperature, and stirred for 10 h. The mixture was poured into H2O and extracted into Et2O (3 × 10 mL). The combined organic layer was dried over MgSO4, concentrated under reduced pressure, and chroatographed on a silica gel column (EtOAc/hexane = 1:2) to afford the acylation product S5 (0.41 g, quantative yield). Under an atmosphere of argon, a mixture of the above-prepared acylation compound S5 (0.41 g, 1.4 mmol), 3-butyn-1-ol (0.14 g, 1.64 mmol), Pd(OAc)2 (5.4 mg, 6.1 mol %), and Bu4NOAc (1.03 g, 3.41 mmol) in acetonitrile (17 mL) was heated at reflux (85°C) for 12 h. After completion of the reaction, the mixture was diluted with water, and extracted with EtOAc. The organic layer was separated, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (CH2Cl2/MeOH = 20:1) to afford indole compound S7 (0.13 g, 55%).
100%	With triethylamine In tetrahydrofuran for 3h;
99%	With triethylamine In tetrahydrofuran at -7 - 20℃;

96%	With TEA In tetrahydrofuran at -15 - 20℃;
96%	With triethylamine In tetrahydrofuran at -15 - 20℃;
95%	With triethylamine In tetrahydrofuran at -15 - 20℃; for 2.5h; Inert atmosphere;
95%	With triethylamine In tetrahydrofuran at -15 - 20℃;
95%	With triethylamine In dichloromethane at -15 - 20℃;
94%	With triethylamine In tetrahydrofuran at -15 - 25℃;
90%	With triethylamine In tetrahydrofuran at -15 - 20℃;
90%	With triethylamine In tetrahydrofuran at -15 - 20℃; for 17h;	4.2.24. 2,2,2-Trifluoro-N-(2-iodophenyl)acetamide ( 37 ) To a solution of 2-iodoaniline (1.0 g, 4.30 mmol) and triethy- lamine (0.7 mL, 4.55 mmol) in THF (10 mL) at -15 °C was slowly added trifluoroacetic anhydride (0.65 mL, 4.30 mmol) in 5 mL of THF. The resulting mixture was stirred for 1 h and then allowed to warm to room temperature and stirred for 16 h. The reaction mixture was then poured into a separatory funnel containing wa- ter (100 mL) and extracted with ethyl acetate (3 ×30 mL). The or- ganic layers were dried over anhydrous Na 2 SO 4 . The solvent was removed under vacuum to give desired product 37 (1.3 g, 90%) as a white solid (Mp: 105-106 °C). 1 H-NMR (400 MHz, CDCl 3 ): 8.29 (s, 1H), 8.21 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 7.6 Hz, 1H), 7.42 (t, J = 7.6 Hz, 1H), 6.98 (t, J = 7.6 Hz, 1H) [34] .
88%	With triethylamine In tetrahydrofuran for 2h; Ambient temperature;
88%	With triethylamine In dichloromethane at 0 - 23℃; for 12h;
82%	With triethylamine In dichloromethane at 0℃; for 1h;
70%	With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃;	6.B 2,2,2-trifluoro-N-(2-iodophenyl)acetamide Example 6B 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 2-Iodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl-4-methyl-pyridine (Aldrich, 1.23 g, 6 mmol) in CH2Cl2 (10 mL) at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3*10 mL). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70%). 1H NMR (300 MHz, CD3OD) δ 7.07-7.12 (m, 1H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1H) ppm. MS (DCl): m/z 316 (M+H)+.
70%	Stage #1: 2-iodophenylamine; trifluoroacetic anhydride With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃; Stage #2: With water In dichloromethane	6B 2,2,2-Trifluoro-N-(2-iodophenyl)acetamide 2-Iodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl4-methyl-pyridine (Aldrich, 1.23 g, 6 mmol) in CH2Cl2 (10 mL) at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3×10 mL). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70%). 1H NMR (300 MHz, CD3OD) δ 7.07-7.12 (m, 1H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1H) ppm. MS (DCl): m/z 316 (M+H)+.
70%	With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃;	6.6B 2-lodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl-4-methyl-pyhdine (Aldrich, 1.23 g, 6 mmol) in CH2CI2 (10 ml_)at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3 x 10 ml_). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70%). 1H NMR (300 MHz, CD3OD) δ 7.07-7.12 (m, 1 H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1 H) ppm. MS (DCI): m/z 316 (M+H)+.
	With triethylamine In dichloromethane at 0 - 20℃;
	With pyridine In dichloromethane at 0 - 20℃; for 6h;

Reference： [1]Hong, Bei-Tao; Chen, Chun-Lin; Fang, Jim-Min; Tsai, Keng-Chang; Wang, Shi-Yun; Huang, Wen-I; Cheng, Yih-Shyun E.; Wong, Chi-Huey [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6647 - 6654]
[2]Aubert, Catherine; Lavisse, Mélanie; Roy, Sebastien [ChemBioChem, 2021, vol. 22, # 14, p. 2424 - 2429]
[3]Benek, Ondrej; Soukup, Ondrej; Pasdiorova, Marketa; Hroch, Lukas; Sepsova, Vendula; Jost, Petr; Hrabinova, Martina; Jun, Daniel; Kuca, Kamil; Zala, Dominykas; Ramsay, Rona R.; Marco-Contelles, José; Musilek, Kamil [ChemMedChem, 2016, p. 1264 - 1269]
[4]Kofink, Christiane C.; Blank, Benoit; Pagano, Sandro; Goetz, Nadine; Knochel, Paul [Chemical Communications, 2007, # 19, p. 1954 - 1956]
[5]Location in patent: experimental part Chen, Yu; Markina, Nataliya A.; Larock, Richard C. [Tetrahedron, 2009, vol. 65, # 44, p. 8908 - 8915]
[6]Zhang, Hanmo; Hay, E. Ben; Geib, Steven J.; Curran, Dennis P. [Journal of the American Chemical Society, 2013, vol. 135, # 44, p. 16610 - 16617]
[7]Song, Hongjian; Liu, Yongxian; Liu, Yuxiu; Wang, Qingmin [Organic Letters, 2014, vol. 16, # 12, p. 3240 - 3243]
[8]Liu, Yongxian; Huang, Yuanqiong; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5337 - 5340]
[9]Cironi, Pablo; Tulla-Puche, Judit; Barany, George; Albericio, Fernando; Alvarez, Mercedes [Organic Letters, 2004, vol. 6, # 9, p. 1405 - 1408]
[10]Kabalka, George W.; Wang, Lei; Pagni, Richard M. [Tetrahedron, 2001, vol. 57, # 38, p. 8017 - 8028]
[11]Lafzi, Ferruh; Kilic, Deryanur; Yildiz, Melike; Saracoglu, Nurullah [Journal of Molecular Structure, 2021, vol. 1241]
[12]Tietze, Lutz F.; Schimpf, Ralph [Chemische Berichte, 1994, vol. 127, # 11, p. 2235 - 2240]
[13]Kwon, Yongseok; Li, Junqi; Reid, Jolene P.; Crawford, Jennifer M.; Jacob, Roxane; Sigman, Matthew S.; Toste, F. Dean; Miller, Scott J. [Journal of the American Chemical Society, 2019, vol. 141, # 16, p. 6698 - 6705]
[14]Arnold, Leggy A.; Luo, Wenchen; Guy, R. Kiplin [Organic Letters, 2004, vol. 6, # 17, p. 3005 - 3007]
[15]Current Patent Assignee: ABBVIE INC - US2005/137184, 2005, A1 Location in patent: Page/Page column 21
[16]Current Patent Assignee: ABBOTT LABORATORIES INC - US2005/137204, 2005, A1 Location in patent: Page/Page column 24
[17]Current Patent Assignee: ABBVIE INC - WO2006/65233, 2006, A1 Location in patent: Page/Page column 55
[18]Kadnikov, Dmitry V.; Larock, Richard C. [Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6772 - 6780]
[19]Min, Kwan Hong; Iqbal, Naeem; Cho, Eun Jin [Organic Letters, 2022, vol. 24, # 4, p. 989 - 994]

2
[ 1945-84-2 ]
[ 143321-89-5 ]
[ 13228-40-5 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3843 - 3846

3
[ 78593-40-5 ]
[ 143321-89-5 ]
[ 99285-62-8 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3843 - 3846

4
[ 42472-69-5 ]
[ 143321-89-5 ]
1-(4-(1H-indol-2-yl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate; Cu[(phen)(PPh₃)2]NO₂ In toluene at 110℃; for 20h;

Reference： [1]Cacchi, Sandro; Fabrizi, Giancarlo; Parisi, Luca M. [Organic Letters, 2003, vol. 5, # 21, p. 3843 - 3846]

5
[ 143321-89-5 ]
[ 768-60-5 ]
[ 5784-95-2 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3843 - 3846

6
[ 108-86-1 ]
[ 143321-89-5 ]
[ 536-74-3 ]
[ 3469-20-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3271 - 3274

7
[ 38222-83-2 ]
[ 615-43-0 ]
[ 143321-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic anhydride; In dichloromethane; water;	Example 6B 2,2,2-Trifluoro-N-(2-iodophenyl)acetamide 2-Iodo-phenylamine (Aldrich, 1.09 g, 5 mmol) was treated with trifluoroacetic anhydride (Aldrich, 1.26 g, 6 mmol) and 2,6-di-tert-butyl-4-methyl-pyridine (Aldrich, 1.23 g, 6 mmol) in CH2Cl2 (10 mL)at room temperature overnight. It was then quenched with with water (5 mL) and extracted with EtOAc (3*10 mL). The extracts were combined and washed with brine (5 mL). The organic solution was concentrated and the title compound was purified by flash chromatography (SiO2, Hexanes/EtOAc, 80:20, Rf. 0.50) as a solid (1.1 g, yield, 70percent). 1H NMR (300 MHz, CD3OD) delta 7.07-7.12 (m, 1H), 7.39-7.47 (m, 2H), 7.95 (dd, J=7.8, 1.3 Hz, 1H) ppm. MS (DCI): m/z 316 (M+H)+.

Reference： [1]Patent: US2005/245531,2005,A1

8
[ 94-02-0 ]
[ 143321-89-5 ]
[ 36779-16-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: ethyl 3-oxo-3-phenylpropionate; 2,2,2-trifluoro-N-(2-iodophenyl)acetamide With copper(l) iodide; caesium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 20℃; Stage #2: With hydrogenchloride In methanol; dimethyl sulfoxide at 60 - 80℃; Further stages.;

Reference： [1]Chen, Yu; Xie, Xiaoan; Ma, Dawei [Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9329 - 9334]

9
[ 143321-89-5 ]
[ 16619-14-0 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13397 - 13418
[2]Tetrahedron Letters,1993,vol. 34,p. 1625 - 1628

10
[ 2818-07-7 ]
[ 143321-89-5 ]
[ 1036350-80-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: pyrrole-2,4-dicarboxylic acid dimethyl ester; 2,2,2-trifluoro-N-(2-iodophenyl)acetamide With copper(l) iodide; potassium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 80℃; for 35h; Stage #2: With water In dimethyl sulfoxide at 60℃; for 12h; Further stages.;

Reference： [1]Yuan, Qiliang; Ma, Dawei [Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 5159 - 5162]

11
[ 143321-89-5 ]
[ 215589-37-0 ]
[ 1176667-08-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 6315 - 6318

12
[ 137-26-8 ]
[ 143321-89-5 ]
[ 4074-74-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h;

Reference： [1]Location in patent: experimental part Pi, Sha-Sha; Zhang, Xing-Guo; Tang, Ri-Yuan; Li, Jin-Heng [Synlett, 2009, # 18, p. 3032 - 3036]

13
[ 143321-89-5 ]
[ 215589-37-0 ]
[ 1224955-45-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3371 - 3380
[2]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1902 - 1908
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4468 - 4476

14
[ 143321-89-5 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1035 - 1038

15
[ 627-19-0 ]
[ 143321-89-5 ]
[ 13228-41-6 ]

Yield	Reaction Conditions	Operation in experiment
38%	With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 80℃; for 144h; Inert atmosphere;

Reference： [1]Wang, Ruiping; Mo, Song; Lu, Yongzhong; Shen, Zengming [Advanced Synthesis and Catalysis, 2011, vol. 353, # 5, p. 713 - 718]

16
[ 4843-44-1 ]
[ 143321-89-5 ]
[ 55968-16-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; <i>L</i>-proline; copper(I) bromide In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere;	General procedure for the synthesis of 3, 4, 5, 7, 8 and 9. General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 °C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 °C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 °C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.

Reference： [1]Ponpandian, Thanasekaran; Muthusubramanian, Shanmugam [Tetrahedron Letters, 2012, vol. 53, # 32, p. 4248 - 4252]

17
[ 3240-10-6 ]
[ 143321-89-5 ]
[ 1211-35-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; <i>L</i>-proline; copper(I) bromide In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere;	General procedure for the synthesis of 3, 4, 5, 7, 8 and 9. General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 °C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 °C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 °C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.

Reference： [1]Ponpandian, Thanasekaran; Muthusubramanian, Shanmugam [Tetrahedron Letters, 2012, vol. 53, # 32, p. 4248 - 4252]

18
[ 25294-65-9 ]
[ 143321-89-5 ]
[ 6127-49-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; L-proline; copper(I) bromide; In dimethyl sulfoxide; at 100℃; for 3h;Inert atmosphere;	General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4248 - 4252

19
[ 29835-28-7 ]
[ 143321-89-5 ]
[ 93716-78-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; L-proline; copper(I) bromide; In dimethyl sulfoxide; at 100℃; for 3h;Inert atmosphere;	General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4248 - 4252

20
[ 704-97-2 ]
[ 143321-89-5 ]
[ 52765-22-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; <i>L</i>-proline; copper(I) bromide In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere;	General procedure for the synthesis of 3, 4, 5, 7, 8 and 9. General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 °C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 °C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 °C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.

Reference： [1]Ponpandian, Thanasekaran; Muthusubramanian, Shanmugam [Tetrahedron Letters, 2012, vol. 53, # 32, p. 4248 - 4252]

21
[ 143321-89-5 ]
[ 637-44-5 ]
[ 948-65-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; <i>L</i>-proline; copper(I) bromide In dimethyl sulfoxide at 100℃; for 3h; Inert atmosphere;	General procedure for the synthesis of 3, 4, 5, 7, 8 and 9. General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 °C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 °C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 °C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.
70%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 110℃; for 12h;

Reference： [1]Ponpandian, Thanasekaran; Muthusubramanian, Shanmugam [Tetrahedron Letters, 2012, vol. 53, # 32, p. 4248 - 4252]
[2]Reddy, C. Bal; Bharti, Richa; Kumar, Sandeep; Das, Pralay [RSC Advances, 2016, vol. 6, # 75, p. 71117 - 71121]

22
[ 107-19-7 ]
[ 143321-89-5 ]
[ 598-74-3 ]
N-((1H-indol-2-yl)methyl)-3-methylbutan-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 9h; Inert atmosphere;

Reference： [1]Cacchi, Sandro; Fabrizi, Giancarlo; Iazzetti, Antonia; Molinaro, Carmela; Verdiglione, Rosanna; Goggiamani, Antonella [Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 1053 - 1059]

23
[ 143321-89-5 ]
[ 536-74-3 ]
[ 579-93-1 ]

Yield	Reaction Conditions	Operation in experiment
55%		A mixture of compound 5a (0.20 mmol), arylacetylene (0.22 mmol), Pd(PPh3)2Cl2 (1.4 mg, 0.002 mmol), CuCl (4.0 mg,0.04 mmol), and Na2CO3 (42 mg, 0.40 mmol) in DMSO (1.0 mL) was stirred at 80 C under Ar for 1 h, then stirred under O2(1 atm). After 24 h, the mixture was quenched with 10% HCl at C and extracted with EtOAc. The organic extracts were washed with H2O and brine, dried over Na2SO4, and then concentrated.The residue was dissolved in saturated NaHCO3, washed with CH2Cl2, and the aqueous fraction was acidified with drop-wise addition of 10% HCl at 0 C and extracted with ethyl acetate. The organic extracts were washed with H2O and brine, dried over Na2SO4, and then concentrated.

Reference： [1]Tetrahedron,2014,vol. 70,p. 5746 - 5751

24
[ 143321-89-5 ]
[ 215589-37-0 ]
N-{2-[(2-amino-5-methylphenyl)ethynyl]phenyl}-2,2,2-trifluoroacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: The appropriate o-(o-aminophenylethynyl) trifluoroacetanilides 5 and o-(oaminophenylethynyl)anilines 15 were prepared, usually in high yields, via a Sonogashiracross-coupling of 2-iodotrifluoroacetanilides or 2-iodoaniline with 2-ethynylanilines.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2411 - 2417
[2]Synthesis,2018,vol. 50,p. 1133 - 1140

25
[ 143321-89-5 ]
[ 215589-37-0 ]
ethyl 4-(2-methyl-6-oxo-5,6-dihydroindolo[1,2-c]quinazolin-12-yl)benzoate [ No CAS ]

Reference： [1]Synthesis,2018,vol. 50,p. 1133 - 1140

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[ CAS No. 143321-89-5 ] {[proInfo.proName]}

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[ 143321-89-5 ] Synthesis Path-Upstream 1~2

[ 143321-89-5 ] Synthesis Path-Downstream 1~25

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