Name: 30955-94-3|1-(5-Iodothiophen-2-yl)ethanone|97%
Brand: Ambeed
SKU: A105302
Price: 17.0 USD
Availability: InStock
Rating: 94 (32 reviews)

1
[ 30955-94-3 ]
[ 383-63-1 ]
[ 326-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; sodium methylate

Reference： [1]Barkley; Levine [Journal of the American Chemical Society, 1951, vol. 73, p. 4625]

2
[ 30955-94-3 ]
[ 60166-85-0 ]

Reference： [1]Chemische Berichte,1886,vol. 19,p. 693
[2]Recueil des Travaux Chimiques des Pays-Bas,1934,vol. 53,p. 643,648
Recueil des Travaux Chimiques des Pays-Bas,1936,vol. 55,p. 991

3
[ 188290-36-0 ]
[ 30955-94-3 ]
[ 3515-18-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	In acetonitrile for 3h; Irradiation;

Reference： [1]D'Auria, Maurizio; Mico, Antonella De; D'Onofrio, Franco; Piancatelli, Giovanni [Journal of the Chemical Society. Perkin transactions I, 1987, p. 1777 - 1780]

4
[ 3140-93-0 ]
[ 30955-94-3 ]
[ 111505-82-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	In acetonitrile for 3h; Irradiation;

Reference： [1]D'Auria, Maurizio; Mico, Antonella De; D'Onofrio, Franco; Piancatelli, Giovanni [Journal of the Chemical Society. Perkin transactions I, 1987, p. 1777 - 1780]

5
[ 1759-28-0 ]
[ 30955-94-3 ]
[ 125972-70-5 ]
[ 125972-84-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4019 - 4025

6
[ 30955-94-3 ]
[ 19432-68-9 ]
methyl 5'-acetyl-2,2'-bithienyl-5-acetate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1245 - 1250

7
[ 30955-94-3 ]
[ 4175-76-2 ]
2-acetyl-5-(2,4-dichloro-5-thiazolyl)thiophene [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1989,vol. 119,p. 381 - 384

8
[ 30955-94-3 ]
5-Trimethylsilyl-2-ethynylthiophene [ No CAS ]
2-Acetyl-5-(5'-trimethylsilyl-2'-thienylethynyl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetonitrile for 6h; Irradiation;

Reference： [1]D'Auria, Maurizio; Tofani, Daniela [Tetrahedron, 1992, vol. 48, # 42, p. 9315 - 9322]

9
[ 30955-94-3 ]
[4-(5-Iodo-thiophene-2-carbonyl)-2-oxy-furazan-3-yl]-(5-iodo-thiophen-2-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With nitric acid In acetonitrile at 65 - 70℃; for 2h;

Reference： [1]Espenbetov, A. A.; Struchkov, Yu. T.; Churkin, Yu. D.; Panfilova, L. V. [Journal of general chemistry of the USSR, 1985, vol. 55, # 7, p. 1392 - 1396][Zhurnal Obshchei Khimii, 1985, vol. 55, # 7, p. 1565 - 1570]

10
[ 88-15-3 ]
[ 30955-94-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	With iodine; bis-[(trifluoroacetoxy)iodo]benzene In tetrachloromethane for 2h;

Reference： [1]D'Auria; Mauriello [Tetrahedron Letters, 1995, vol. 36, # 27, p. 4883 - 4884]

11
[ 30955-94-3 ]
C₄H₃SCOC⁽²⁾HH₂ [ No CAS ]
C₆H₅⁽²⁾HOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-acetyl-5-iodothiophene With N,N-dimethyl acetamide; neopentylmagnesium bromide In tetrahydrofuran at -80℃; for 1h; Stage #2: With deuteroacetic acid In tetrahydrofuran at -78℃; Title compound not separated from byproducts;

Reference： [1]Kneisel, Florian Felix; Knochel, Paul [Synlett, 2002, # 11, p. 1799 - 1802]

12
[ 30955-94-3 ]
[ 72824-04-5 ]
1-(5-allyl-thiophen-2-yl)-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With cesium fluoride In tetrahydrofuran Heating;

Reference： [1]Kotha, Sambasivarao; Behera, Manoranjan; Shah, Vrajesh R. [Synlett, 2005, # 12, p. 1877 - 1880]

13
[ 30955-94-3 ]
[ 619-44-3 ]
4-(5-acetyl-2-thiophenyl)benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: 2-acetyl-5-iodothiophene With diisopropyl zinc; lithium pentane-2,4-dionate In 1-methyl-pyrrolidin-2-one; diethyl ether at 0℃; for 5h; Stage #2: methyl 4-iodobenzoate With trifuran-2-yl-phosphane In 1-methyl-pyrrolidin-2-one; diethyl ether at 20℃; for 5h;

Reference： [1]Kneisel, Florian F.; Leuser, Helena; Knochel, Paul [Synthesis, 2005, # 15, p. 2625 - 2629]

14
[ 30955-94-3 ]
[ 3680-93-1 ]
3-(5-dimethylamino-2-furyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.5%	With potassium hydroxide In ethanol; water at 20℃; for 0.5h;

Reference： [1]Ono, Masahiro; Hori, Miyuki; Haratake, Mamoru; Tomiyama, Takami; Mori, Hiroshi; Nakayama, Morio [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 19, p. 6388 - 6396]

15
[ 30955-94-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6388 - 6396

16
[ 30955-94-3 ]
[ 555-16-8 ]
(E)-1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-2-propen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.1%	With potassium hydroxide In ethanol; water at 20℃; for 0.5h;

Reference： [1]Ono, Masahiro; Hori, Miyuki; Haratake, Mamoru; Tomiyama, Takami; Mori, Hiroshi; Nakayama, Morio [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 19, p. 6388 - 6396]

17
[ 30955-94-3 ]
[ 100-10-7 ]
[ 948841-08-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium hydroxide In ethanol; water at 20℃; for 48h;	4.3.2. General procedure for the synthesis of the chalcones General procedure: Chalcones 2a-c and 3a-c were obtained by a classical Claisen-Schmidt condensation in basic ethanolic media. In a typical procedure,the corresponding aldehyde (1 mmol) and 2-acetyl-5-halothiophene(1 mmol) were suspended in EtOH (5 ml) at room temperature. To thismixture was added dropwise a 10% aq. KOH solution (2.5 ml) underconstant stirring, with an observed color change upon complete additionof base (typically orange-red). The reaction mixture was thenstirred at room temperature for 48 h, after which an intensely coloredorange/red precipitate had formed. To the suspension was added colddistilled water (ca. 5 ml) and the precipitate was filtered, washed withdistilled water (3 × 5 ml) and ice-cold MeOH (2 × 5 ml), then driedunder vacuum, affording pure compounds 2a-c. Compounds 3a-c wererecrystallized from an ethanol/CHCl3/water (3:3:1) mixture and driedunder vacuum.
69.3%	With potassium hydroxide In ethanol; water at 20℃; for 0.5h;
62.1%	With potassium hydroxide In ethanol; water at 20℃; for 6h; Cooling with ice;	1 Synthesis of (E) -3-(4-(dimethylamino)phenyl)-1-(5-iodothiophen-2-yl)prop-2-en-1-one (1) Synthesis of (E) -3-(4-(dimethylamino)phenyl)-1-(5-iodothiophen-2-yl)prop-2-en-1-one (1) 256 mg (1 mmol) of 5-acetyl-2-iodothiophene and 149 mg (1 mmol) of 4-dimethylaminobenzaldehyde were dissolved in ethanol (20 mL), and 10% aqueous potassium hydroxide (30 mL) was added to the mixture with ice cooling. A reaction was allowed at room temperature for 6 h, followed by addition of 30 mL of purified water, and the precipitated crystals were filtered by suction. The crystals were washed with 50% aqueous ethanol and dried to obtain target Compound 1. Yield 238 mg (yield rate 62.1%). 1H NMR (300 MHz, CDCl3) δ 3.06 (s, 6H), 6.69 (d, J = 9.0 Hz, 2H), 7.11 (d, J = 15.6 Hz, 1H), 7.32 (d, J = 3.9 Hz, 1H), 7.45 (d, J = 3.9 Hz, 1H), 7.54 (d, J = 9.0 Hz, 2H), 7.81 (d, J = 15.3 Hz, 2H).

Reference： [1]Echevarria, Lorenzo; Fernández-Terán, Ricardo; Hernández, Florencio Eloy; Sucre-Rosales, Estefanía; Urdaneta, Neudo [Chemical Physics, 2020, vol. 537]
[2]Ono, Masahiro; Hori, Miyuki; Haratake, Mamoru; Tomiyama, Takami; Mori, Hiroshi; Nakayama, Morio [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 19, p. 6388 - 6396]
[3]Current Patent Assignee: NAGASAKI UNIVERSITY - EP2030635, 2009, A1 Location in patent: Page/Page column title page; 20; 46

18
[ 925430-09-7 ]
[ 30955-94-3 ]
[ 893738-59-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h;

Reference： [1]Gagnon, Alexandre; Duplessis, Martin; Alsabeh, Pamela; Barabe, Francis [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3604 - 3607]

19
[ 30955-94-3 ]
[ 625-81-0 ]
[ 684215-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium pentane-2,4-dionate In diethyl ether reaction of Zn(iPr)2 with IC4H2SCOMe in presence of Li(acac) in mixt. ofEt2O and N-methylpyrrolidinone; detn. by gas chromy.;

Reference： [1]Kneisel, Florian F.; Dochnahl, Maximilian; Knochel, Paul [Angewandte Chemie - International Edition, 2004, vol. 43, # 8, p. 1017 - 1021]

20
[ 30955-94-3 ]
[ 401-81-0 ]
[ 893735-18-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 2-acetyl-5-iodothiophene With indium; hepatdecane; lithium chloride In tetrahydrofuran at 30℃; for 0.333333h; Stage #2: m-trifluoromethylphenyl iodide With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 40℃; for 4h; Inert atmosphere;

Reference： [1]Chen, Yi-Hung; Knochel, Paul [Angewandte Chemie - International Edition, 2008, vol. 47, # 40, p. 7648 - 7651]

21
[ 30955-94-3 ]
aqueous potassium hydroxide [ No CAS ]
[ 555-16-8 ]
(E)-1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-2-propen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.1%	In ethanol	2 Synthesis of 1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-prop-2-en-1-one (11) Synthesis of 1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-prop-2-en-1-one (11) 2-Acetyl-5-iodothiophene (486 mg, 1.93 mmol) and 4-nitrobenzaldehyde (296 mg, 1.96 mmol) were dissolved in ethanol (10 mL), and 10% aqueous potassium hydroxide (6 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 30 min, and the precipitates were collected by filtration and washed with 50% ethanol to obtain Compound 11. Yield 625 mg (yield rate 84.1%). 1H NMR (300 MHz, CDCl3) δ 7.38-7.43 (m, 2H), 7.51 (d, J=4.2 Hz, 1H), 7.78 (d, J=8.4 Hz, 2H), 7.84 (d, J=15.6 Hz, 1H), 8.29 (d, J=9 Hz, 2H).

Reference： [1]Current Patent Assignee: NAGASAKI UNIVERSITY - US2010/278733, 2010, A1

22
[ 30955-94-3 ]
aqueous potassium hydroxide [ No CAS ]
[ 100-10-7 ]
[ 948841-08-5 ]

Yield	Reaction Conditions	Operation in experiment
69.3%	In ethanol	2 Synthesis of 1-(5-iodo-2-thienyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one (14) Synthesis of 1-(5-iodo-2-thienyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one (14) 2-Acetyl-5-iodothiophene (260 mg, 1.03 mmol) and 4-dimethylaminobenzaldehyde (159 mg, 1.07 mmol) were dissolved in ethanol (15 mL), and 10% aqueous potassium hydroxide (15 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, and then the precipitates were collected by filtration and washed with 50% ethanol to obtain Compound 14. Yield 274 mg (yield rate 69.3%). 1H NMR (300 MHz, CDCl3) δ 3.05 (s, 6H), 6.79 (d, J=8.7 Hz, 2H), 7.11 (d, J=15.3 Hz, 1H), 7.32 (d, J=3.9 Hz, 1H), 7.45 (d, J=3.9 Hz, 1H), 7.54 (d, J=8.7 Hz, 2H), 7.81 (d, J=15 Hz, 1H). MS m/z 383 (M+)
	In ethanol	1 Synthesis of (E)-3-(4-(dimethylamino)phenyl)-1-(5-iodothiophen-2-yl)prop-2-en-1-one (1) Synthesis of (E)-3-(4-(dimethylamino)phenyl)-1-(5-iodothiophen-2-yl)prop-2-en-1-one (1) 256 mg (1 mmol) of 5-acetyl-2-iodothiophene and 149 mg (1 mmol) of 4-dimethylaminobenzaldehyde were dissolved in ethanol (20 mL), and 10% aqueous potassium hydroxide (30 mL) was added to the mixture with ice cooling. A reaction was allowed at room temperature for 6 h, followed by addition of 30 mL of purified water, and the precipitated crystals were filtered by suction. The crystals were washed with 50% aqueous ethanol and dried to obtain target Compound 1. Yield 238 mg (yield rate 62.1%). 1H NMR (300 MHz, CDCl3) δ 3.06 (s, 6H), 6.69 (d, J=9.0 Hz, 2H), 7.11 (d, J=15.6 Hz, 1H), 7.32 (d, J=3.9 Hz, 1H), 7.45 (d, J=3.9 Hz, 1H), 7.54 (d, J=9.0 Hz, 2H), 7.81 (d, J=15.3 Hz, 2H).

Reference： [1]Current Patent Assignee: NAGASAKI UNIVERSITY - US2010/278733, 2010, A1
[2]Current Patent Assignee: NAGASAKI UNIVERSITY - US2010/278733, 2010, A1

23
[ 30955-94-3 ]
[ 555-16-8 ]
1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.1%	With potassium hydroxide In ethanol; water at 20℃; for 0.5h;	2 Synthesis of 1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-prop-2-en-1-one (11) Synthesis of 1-(5-iodo-2-thienyl)-3-(4-nitrophenyl)-prop-2-en-1-one (11) 2-Acetyl-5-iodothiophene (486 mg, 1.93 mmol) and 4-nitrobenzaldehyde (296 mg, 1.96 mmol) were dissolved in ethanol (10 mL), and 10% aqueous potassium hydroxide (6 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 30 min, and the precipitates were collected by filtration and washed with 50% ethanol to obtain Compound 11. Yield 625 mg (yield rate 84.1%). 1H NMR (300 MHz, CDCl3) δ 7.38-7.43 (m, 2H), 7.51 (d, J = 4.2 Hz, 1H), 7.78 (d, J = 8.4 Hz, 2H), 7.84 (d, J = 15.6 Hz, 1H), 8.29 (d, J = 9 Hz, 2H).

Reference： [1]Current Patent Assignee: NAGASAKI UNIVERSITY - EP2030635, 2009, A1 Location in patent: Page/Page column 23; 48

24
[ 30955-94-3 ]
[ 100-10-7 ]
1-(5-iodo-2-thienyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.3%	With potassium hydroxide In ethanol; water at 20℃; for 3h;	2 Synthesis of 1-(5-iodo-2-thienyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one (14) Synthesis of 1-(5-iodo-2-thienyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one (14) 2-Acetyl-5-iodothiophene (260 mg, 1.03 mmol) and 4-dimethylaminobenzaldehyde (159 mg, 1.07 mmol) were dissolved in ethanol (15 mL), and 10% aqueous potassium hydroxide (15 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, and then the precipitates were collected by filtration and washed with 50% ethanol to obtain Compound 14. Yield 274 mg (yield rate 69.3%). 1H NMR (300 MHz, CDCl3) δ 3.05 (s, 6H), 6.79 (d, J = 8.7 Hz, 2H), 7.11 (d, J = 15.3 Hz, 1H), 7.32 (d, J = 3.9 Hz, 1H), 7.45 (d, J = 3.9 Hz, 1H), 7.54 (d, J = 8.7 Hz, 2H), 7.81 (d, J = 15 Hz, 1H). MS m/z 383 (M+).

Reference： [1]Current Patent Assignee: NAGASAKI UNIVERSITY - EP2030635, 2009, A1 Location in patent: Page/Page column 24; 48

25
[ 30955-94-3 ]
[ 3680-93-1 ]
3-(5-dimethylamino-2-furyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.5%	With potassium hydroxide In ethanol; water at 20℃; for 1.5h;	2 Synthesis of 3-(5-dimethylamino-2-furyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one (36) Synthesis of 3-(5-dimethylamino-2-furyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one (36) 2-Acetyl-5-iodothiophene (123 mg, 0.49 mmol) and Compound 28 (71 mg, 0.51 mmol) were dissolved in ethanol (5 mL), and 10% aqueous potassium hydroxide (2 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 90 min, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/3) as an elution solvent to obtain Compound 36. Yield 21 mg (yield rate 11.5%). 1H NMR (300 MHz, CDCl3) δ 3.04 (s, 6H), 5.22 (d, J = 3.6 Hz, 1H), 6.73 (d, J = 14.4 Hz, 1H), 6.79 (d, J = 3.9 Hz, 1H), 7.29 (d, J = 3.9 Hz, 1H), 7.50 (d, J = 3.9 Hz, 1H), 7.45 (d, J = 14.7 Hz, 1H). MS m/z 373 (M+).

Reference： [1]Current Patent Assignee: NAGASAKI UNIVERSITY - EP2030635, 2009, A1 Location in patent: Page/Page column 27; 50

26
[ 30955-94-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.9%	With potassium hydroxide; In ethanol; water; at 20℃; for 3.0h;	Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one (37) 2-Acetyl-5-iodothiophene (123 mg, 0.49 mmol) and Compound 30 (76 mg, 0.49 mmol) were dissolved in ethanol (3 mL), and 10% aqueous potassium hydroxide (1 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain compound 37. Yield 15 mg (yield rate 7.9%). 1H NMR (300 MHz, CDCl3) delta 3.07 (s, 6H), 5.85 (d, J = 4.2 Hz, 1H), 6.63 (d, J = 14.7 Hz, 1H), 7.15 (d, J = 4.5 Hz, 1H), 7.29 (d, J = 3.9 Hz, 1H), 7.38 (d, J = 4.2 Hz, 1H), 7.87 (d, J = 14.7 Hz, 1H). MS m/z 389 (M+).

Reference： [1]Patent: EP2030635,2009,A1 .Location in patent: Page/Page column 27; 50

27
[ 30955-94-3 ]
[ 82072-23-9 ]
[ 1155702-64-9 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 2236 - 2239

28
[ 30955-94-3 ]
[ 73568-27-1 ]
[ 1185844-21-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide In methanol; water at 20℃; for 2h;
72%	With sodium hydroxide In methanol; water at 20℃; for 2h;
	With sodium hydroxide In ethanol; water

Reference： [1]Location in patent: experimental part Rizvi, Syed Umar Farooq; Siddiqui, Hamid Latif; Parvez, Masood; Ahmad, Matloob; Siddiqui, Waseeq Ahmad; Yasinzai, Muhammad Masoom [Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 3, p. 301 - 306]
[2]Location in patent: experimental part Rizvi, Umar Farooq; Siddiqui, Hamid Latif; Ahmad, Saeed; Ahmad, Matloob; Parvez, Masood [Acta Crystallographica, Section C: Crystal Structure Communications, 2008, vol. 64, # 10, p. o547-o549]
[3]Rizvi, Syed Umar Farooq; Ahmad, Matloob; Bukhari, Mujahid Hussain; Montero, Catherine; Chatterjee, Payel; Detorio, Mervi; Schinazi, Raymond F. [Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 402 - 407]

29
[ 30955-94-3 ]
aqueous potassium hydroxide [ No CAS ]
[ 24372-46-1 ]
3-(S-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.9%	With sodium hydroxide; In ethanol; hexane; ethyl acetate;	Synthesis of 3-(S-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one (37) 2-Acetyl-5-iodothiophene (123 mg, 0.49 mmol) and Compound 30 (76 mg, 0.49 mmol) were dissolved in ethanol (3 mL), and 10% aqueous potassium hydroxide (1 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain compound 37. Yield 15 mg (yield rate 7.9%). 1H NMR (300 MHz, CDCl3) delta 3.07 (s, 6H), 5.85 (d, J=4.2 Hz, 1H), 6.63 (d, J=14.7 Hz, 1H), 7.15 (d, J=4.5 Hz, 1H), 7.29 (d, J=3.9 Hz, 1H), 7.38 (d, J=4.2 Hz, 1H), 7.87 (d, J=14.7 Hz, 1H). MS m/z 389 (M+).

Reference： [1]Patent: US2010/278733,2010,A1

30
[ 30955-94-3 ]
[ 73568-29-3 ]
[ 1253278-31-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide In methanol; water at 20℃; for 2h;
	With sodium hydroxide In ethanol; water

Reference： [1]Location in patent: experimental part Rizvi, Syed Umar Farooq; Siddiqui, Hamid Latif; Parvez, Masood; Ahmad, Matloob; Siddiqui, Waseeq Ahmad; Yasinzai, Muhammad Masoom [Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 3, p. 301 - 306]
[2]Rizvi, Syed Umar Farooq; Ahmad, Matloob; Bukhari, Mujahid Hussain; Montero, Catherine; Chatterjee, Payel; Detorio, Mervi; Schinazi, Raymond F. [Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 402 - 407]

31
[ 30955-94-3 ]
[ 1265602-75-2 ]
[ 1265602-86-5 ]

Yield	Reaction Conditions	Operation in experiment
37%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Gagnon, Alexandre; Albert, Vincent; Duplessis, Martin [Synlett, 2010, # 19, p. 2936 - 2940]

32
[ 30955-94-3 ]
[ 36282-40-3 ]
[ 18494-73-0 ]
[ 6161-50-8 ]
[ 893735-15-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: (3-methoxyphenyl)magnesium bromide With bismuth(III) chloride Stage #2: 2-acetyl-5-iodothiophene With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;

Reference： [1]Rao, Maddali L. N.; Banerjee, Debasis; Dhanorkar, Ritesh J. [Synlett, 2011, # 9, p. 1324 - 1330]

33
[ 30955-94-3 ]
[ 873-77-8 ]
[ 51335-90-1 ]
[ 18494-73-0 ]
[ 2050-68-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: (4-chlorphenyl)magnesium bromide With bismuth(III) chloride Stage #2: 2-acetyl-5-iodothiophene With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;

Reference： [1]Rao, Maddali L. N.; Banerjee, Debasis; Dhanorkar, Ritesh J. [Synlett, 2011, # 9, p. 1324 - 1330]

34
[ 30955-94-3 ]
[ 100-58-3 ]
[ 1665-41-4 ]
[ 18494-73-0 ]
[ 92-52-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: phenylmagnesium bromide With bismuth(III) chloride Stage #2: 2-acetyl-5-iodothiophene With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;

Reference： [1]Rao, Maddali L. N.; Banerjee, Debasis; Dhanorkar, Ritesh J. [Synlett, 2011, # 9, p. 1324 - 1330]

35
[ 30955-94-3 ]
[ 13139-86-1 ]
[ 13918-67-7 ]
[ 18494-73-0 ]
[ 2132-80-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 4-methoxyphenyl magnesium bromide With bismuth(III) chloride Stage #2: 2-acetyl-5-iodothiophene With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;

Reference： [1]Rao, Maddali L. N.; Banerjee, Debasis; Dhanorkar, Ritesh J. [Synlett, 2011, # 9, p. 1324 - 1330]

36
[ 30955-94-3 ]
[ 4294-57-9 ]
[ 51335-91-2 ]
[ 18494-73-0 ]
[ 613-33-2 ]

Reference： [1]Synlett,2011,p. 1324 - 1330

37
[ 30955-94-3 ]
[ 352-13-6 ]
[ 18494-73-0 ]
[ 886361-46-2 ]
[ 398-23-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 4-flourophenylmagnesium bromide With bismuth(III) chloride Stage #2: 2-acetyl-5-iodothiophene With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;

Reference： [1]Rao, Maddali L. N.; Banerjee, Debasis; Dhanorkar, Ritesh J. [Synlett, 2011, # 9, p. 1324 - 1330]

38
[ 6310-09-4 ]
[ 30955-94-3 ]

Yield	Reaction Conditions	Operation in experiment
55 %Chromat.	Stage #1: 2-acetyl-5-chlorothiophene With indium; chloro-trimethyl-silane; bathophenanthroline; ethylene dibromide; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 80 - 100℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Adak, Laksmikanta; Yoshikai, Naohiko [Journal of Organic Chemistry, 2011, vol. 76, # 18, p. 7563 - 7568]

39
[ 30955-94-3 ]
[ 95-92-1 ]
ethyl 2-hydroxy-4-(5-iodothiophen-2-yl)-4-oxobut-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 2-acetyl-5-iodothiophene; oxalic acid diethyl ester With sodium ethanolate In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water for 0.5h;	4.2. General procedure for the preparation of α,γ-diketo esters [25] General procedure: Following the reported procedure refPreviewPlaceHolder[25], sodium ethoxide (0.43 g, 6.30 mmol) was added into a well stirred mixture of appropriate acetyl derivatives (3.12 mmol) and diethyl oxalate (0.92 g, 6.24 mmol) in anhydrous THF (15 mL) under nitrogen atmosphere. The reaction mixture was stirred at room temperature and upon completion of the reaction, was poured into n-hexane (50 mL). The precipitates were collected and then vigorously stirred in 1N HCl (30 mL) for 30 min. The resultant solid formed was filtered, washed with water, and dried under vacuum. The crude mass obtained was further dissolved in ethyl acetate and reprecipitated with hexane to obtain desired esters 1-20 and 22-24.

Reference： [1]Location in patent: experimental part Bhatt, Aaditya; Gurukumar; Basu, Amartya; Patel, Maulik R.; Kaushik-Basu, Neerja; Talele, Tanaji T. [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5138 - 5145]

40
[ 30955-94-3 ]
[ 73568-26-0 ]
[ 1313405-71-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide In methanol; water at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Rizvi, Syed Umar Farooq; Siddiqui, Hamid Latif; Ahmad, Muhammad Nisar; Ahmad, Matloob; Bukhari, Mujahid Hussain [Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1322 - 1333]

41
[ 30955-94-3 ]
[ 68236-21-5 ]
[ 1313405-57-0 ]