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Product Details of [ 21298-55-5 ]

CAS No. :21298-55-5 MDL No. :MFCD00006214
Formula : C9H7NS Boiling Point : -
Linear Structure Formula :- InChI Key :MINKMXOCFYGGKA-UHFFFAOYSA-N
M.W : 161.22 Pubchem ID :88862
Synonyms :

Calculated chemistry of [ 21298-55-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.55
TPSA : 41.13 Ų

Pharmacokinetics

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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.19
Log Po/w (WLOGP) : 2.81
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 2.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.206 mg/ml ; 0.00128 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.331 mg/ml ; 0.00205 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.8
Solubility : 0.0256 mg/ml ; 0.000158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 21298-55-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21298-55-5 ]

* 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.

  • Downstream synthetic route of [ 21298-55-5 ]

[ 21298-55-5 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 21298-55-5 ]
  • [ 74-85-1 ]
  • [ 201230-82-2 ]
  • 1-(3-Pyridin-2-yl-thiophen-2-yl)-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With dodecacarbonyl-triangulo-triruthenium In toluene at 160℃; for 40h;
88% In N,N-dimethyl acetamide at 160℃; for 10h;
  • 2
  • [ 24244-60-8 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
83% Example 5 Synthesis of 2-(3'-thienyl)pyridine Tetrahydrofuran (10ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 3-bromothiophene (2.67 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (1.83 g, yield 83% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) having the following analytical data as a colorless oil. 1H-NMR spectrum (CDCl3) delta: 7.14-7.19 (m, 1H), 7.39 (dd, 1H, J=3.2 Hz, 5.0 Hz), 7.60-7.73 (m, 3H), 7.90 (dd, 1H, J=0.8 Hz, 3.2 Hz), 8.60-8.63 (m, 1H)
  • 3
  • [ 109-09-1 ]
  • [ 6165-69-1 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
99% With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; tetrabutylammomium bromide; sodium hydrogencarbonate In water for 1h; Reflux;
98% With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h;
96% With Pd(Cy*Phine)2Cl2 ; potassium hydroxide In butan-1-ol at 100℃; for 1h; Glovebox; Inert atmosphere; Schlenk technique;
93% With potassium carbonate In butan-1-ol at 100℃; for 14h;
93% With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h;
With potassium phosphate In ethanol; water at 100℃; for 20h; Sealed tube;
With potassium phosphate; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1'-biphenyl)[2-(2-amino-1,1’-biphenyl)]palladium(II)methanesulfonate In tetrahydrofuran; water at 65℃; Inert atmosphere; Flow reactor;

  • 4
  • [ 21298-55-5 ]
  • [ 4713-59-1 ]
  • [ 105102-78-1 ]
YieldReaction ConditionsOperation in experiment
83% With n-butyllithium In diethyl ether; hexane byproducts: LiBr; to a soln. of 2-(3-thienyl)pyridine in dry ether was added a n-BuLi soln. in hexane dropwise at room temp. under N2, stirred for ca. 1 h, dropwise addn. of a soln. of Ph2SnBr2 in dry ether, refluxed for 4 h; soln. filtered, filtrate concd., product pptd. with hexane; elem. anal.;
  • 5
  • [ 21298-55-5 ]
  • [ 10521-96-7 ]
  • [ 945721-47-1 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 3-(2-pyridyl)thiophene; styryl acetate In toluene at 20℃; for 50h; Heating / reflux; Stage #2: With triethylamine In toluene at 20℃; 8 EXAMPLE 8 Production of 2-(2-styrylthiophen-3-yl)-pyridine A teflon-coated magnetic stirring rod was placed in a 10 mL two-necked flask which was then equipped with a reflux condenser. The reflux condenser was connected to a pressure reduced/nitrogen line and the whole apparatus was dried with heating under reduced pressure. Thereafter N2 gas was charged in the reaction apparatus and the whole reaction apparatus was purged with nitrogen. The reaction vessel was left to cool to room temperature, then, Ru(cod)(cot) complex (0.05 mmol, 15.8 mg), 2-(thiophen-3-yl)-pyridine (1 mmol, 161.2 mg), styryl acetate (3 mmol, 486.6 mg) and toluene (1.5 mL) were added. The mixture was heated by an oil bath and reacted under reflux condition for 50 hours. 50 hours after, the reaction solution was left to cool to room temperature, then, triethylamine (0.3 mL) was added. Isolation of the product was carried out by silica gel column chromatography (i.d.=30 mm; length=170-250 mm; hexane:EtOAc:Et3N=9:1:0.1; 25 mL each). A subject substance 2-(2-styryl-thiophen-3-yl)-pyridine was obtained with a yield of 89%. 1H NMR (CDCl3) d 7.066 (d, J=16.5 Hz, 1H, Vinyl H), 7.19-7.60 (m, 10H, ArH, Vinyl H), 7.736 (td, J=7.6 Hz, J=1.9. Hz, 1H, ArH), 8.693 (d, J=4.9 Hz, 1H, ArH) MS m/z (% relative intensity) 263 (M+, 8), 187 (12), 186 (100), 51 (13)
  • 6
  • [ 6165-69-1 ]
  • [ 25795-97-5 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
62% With potassium phosphate monohydrate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; palladium diacetate In toluene at 20 - 110℃; Inert atmosphere;
  • 7
  • [ 6165-69-1 ]
  • [ 57785-86-1 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
87% With potassium phosphate monohydrate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; palladium diacetate In toluene at 20 - 110℃; Inert atmosphere;
  • 8
  • [ 10486-61-0 ]
  • pyridin-2-ylzinc(II) bromide [ No CAS ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
85% With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
  • 9
  • [ 17249-80-8 ]
  • [ 81745-83-7 ]
  • [ 21298-55-5 ]
  • 10
  • [ 21298-55-5 ]
  • [ 104-92-7 ]
  • [ 1310709-11-5 ]
YieldReaction ConditionsOperation in experiment
82% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-Adamantanecarboxylic acid; potassium carbonate In m-xylene at 120℃; for 22h; Inert atmosphere;
  • 11
  • [ 21298-55-5 ]
  • [ 1345883-70-6 ]
YieldReaction ConditionsOperation in experiment
88% With oxygen; copper diacetate; silver nitrate In 1,2,3-trichloropropane at 130℃; for 24h; regioselective reaction;
  • 12
  • [ 109-04-6 ]
  • lithium triisopropyl 3-thiophenylborate [ No CAS ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
87% With potassium phosphate; chloro-(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)]palladium(II) In tetrahydrofuran; water at 40℃; for 2h; Inert atmosphere;
  • 13
  • [ 109-04-6 ]
  • [ 6165-69-1 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
97% With bis(η3-allyl-μ-chloropalladium(II)); N1,N1,N2,N2-tetrakis[(diphenylphosphino)methyl]ethane-1,2-diamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 110℃; for 24h; Inert atmosphere;
94% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 18h; Inert atmosphere; Sealed tube; 2-(Thiophen-3-yl)pyridine (3z) Following a literature known procedure14 a 10 mL crimp vial was charged with 3-thienylboronic acid(130 mg, 1.01 mmol, 1.2 equiv.), K2CO3 (326 mg, 2.36 mmol, 2.8 equiv.), [Pd(PPh3)2Cl2] (29.6 mg,0.042 mmol, 0.05 equiv.), DME (2.5 mL) and water (1.17 mL). The vial was sealed with an aluminium crimpseal with septum and argon was bubbled through the solution for 10 minutes. Bromopyridine (81 μL,0.842 mmol, 1 equiv.) was added via syringe and the reaction was stirred in a pre-heated heating block for18 hrs at 80 °C. The reaction was allowed to cool to ambient temperature, was quenched by adding waterand was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The crude product was purified by flash silica gel columnchromatography using a mixture of hexanes/EtOAc and was obtained as colorless oil (127 mg, 0.79 mmol,94%).
92% With [(t-Bu)3PH]BF4; palladium diacetate; sodium hydroxide at 20℃; for 0.0833333h; Inert atmosphere; Glovebox;
92% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; isopropyl alcohol at 80℃; for 0.666667h; Microwave irradiation;
76% With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; potassium carbonate In water at 80℃; for 24h; Inert atmosphere; Micellar solution; Green chemistry; 2.2.1. General procedure for the synthesis of thienylpyridines isomers (2-7) starting from thiophenes 1a-1b in micellar medium General procedure: In a 5 mL MW vial, purged with Argon for 15 min, CTAB (219 mg, 0.6 mmol), K2CO3 (278 mg, 2 mmol), 2- or 3-thiopheneboronic acid (256 mg, 2 mmol) and Pd catalyst (0.025 mmol) were introduced. The vial was purged for further 5 min and 4 mL of degassed water was added. The proper bromopyridine isomer (158 mg, 1 mmol) was added, and in the case of a 4-bromopyridine hydrocloride, NaOH (powder, 44 mg, 1.1 mmol) was added to release the pyridine in solution as a free base. The use of only one more additional equivalent of K2CO3 was not enough to make the 4-bromopyridine hydrocloride able to react considerably. The mixture was stirred and sonicated to obtain a homogeneous solution that was introduced into a pre-heated oil bath for 24 h or reacted in a MW reactor for 30 min at the proper temperature. When the starting material was consumed, the reaction was diluted with further 5 mL of water and extracted with ethyl acetate (3 5ml). For comparison a few solvents were used: CH2Cl2 (5x5mL) or Et2O (2-3x5ml) and EtOAc (2-3x5ml), with comparable efficiencies. The organic layers were then collected, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography of the crude residue afforded the desired products 2-7. Yields of isolated products are based on the starting pyridine.
74% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 17h; Inert atmosphere; Reflux;
51% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 18h;
50% With Pd(memantine)<SUB>2</SUB>Cl<SUB>2</SUB>; sodium hydroxide In ethanol at 80℃; for 24h; 4.2 General procedure for the Suzuki reaction General procedure: In the reaction tube with a magnetic bar was added the solution of aryl bromides (0.5 mmol) and phenylboronic acid (91 mg, 0.75 mmol), NaOH (24 mg, 0.6 mmol), complex 1 (0.0001-0.02 mol%, dissolved in DMA) and ethanol (3 mL). After stirred for the required time in the preset conditions, the reaction mixture was cooled to room temperature, and then quenched by 1 mL brine and 3 mL water, and extracted with ethyl acetate (3×5 mL). The combined organic layer was dried over anhydrous MgSO4 and the filtrate was concentrated to dryness under reduced pressure. The crude products were purified by column chromatography (petroleum ether, ethyl acetate) on silica gel.
With potassium phosphate In ethanol; water at 100℃; for 6h; Sealed tube;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 95℃; for 18h;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 16h; Inert atmosphere; Schlenk technique; Reflux;

Reference: [1]Wang, Kun; Fu, Qi; Zhou, Rong; Zheng, Xueli; Fu, Haiyan; Chen, Hua; Li, Ruixiang [Applied Organometallic Chemistry, 2013, vol. 27, # 4, p. 232 - 238]
[2]Bergonzini, Giulia; Brandt, Peter; Fricke, Florian; Johansson, Magnus J.; König, Burkhard; Schmalzbauer, Matthias; Svejstrup, Thomas D. [Chem, 2020, vol. 6, # 10, p. 2658 - 2672]
[3]Zou, Yinjun; Yue, Guizhou; Xu, Jianwei; Zhou, Jianrong [European Journal of Organic Chemistry, 2014, vol. 2014, # 27, p. 5901 - 5905]
[4]Pinheiro, Pedro De Sena Murteira; Rodrigues, Daniel Alencar; Alves, Marina Amaral; Tinoco, Luzineide Wanderley; Ferreira, Glaucio Braga; De Sant'Anna, Carlos Mauricio Rabello; Fraga, Carlos Alberto Manssour [New Journal of Chemistry, 2018, vol. 42, # 1, p. 497 - 505]
[5]Quagliotto; Barbero; Barolo; Buscaino; Carfora; Prosperini; Viscardi [Dyes and Pigments, 2017, vol. 137, p. 468 - 479]
[6]Ni, Shengjun; Hribersek, Matic; Baddigam, Swarna K.; Ingner, Fredric J. L.; Orthaber, Andreas; Gates, Paul J.; Pilarski, Lukasz T. [Angewandte Chemie - International Edition, 2021, vol. 60, # 12, p. 6660 - 6666][Angew. Chem., 2021, vol. 133, # 12, p. 6734 - 6740,7]
[7]Jiménez-Aberasturi, Xabier; Leicea, Eztizen; Lete, Esther; Lete, Marta G.; Santiago, Carlos; Sotomayor, Nuria [Organic and Biomolecular Chemistry, 2022, vol. 20, # 4, p. 852 - 861]
[8]Wu, Qinxu; Wu, Leilei; Zhang, Lei; Fu, Haiyan; Zheng, Xueli; Chen, Hua; Li, Ruixiang [Tetrahedron, 2014, vol. 70, # 21, p. 3471 - 3477]
[9]Donga, Zhongmin; Yea, Zhibin [Advanced Synthesis and Catalysis, 2014, vol. 356, # 16, p. 3401 - 3414]
[10]Pawar, Amit B.; Chang, Sukbok [Organic Letters, 2015, vol. 17, # 3, p. 660 - 663]
[11]Zhao, Dongbing; Kim, Ju Hyun; Stegemann, Linda; Strassert, Cristian A.; Glorius, Frank [Angewandte Chemie - International Edition, 2015, vol. 54, # 15, p. 4508 - 4511][Angew. Chem., 2015, vol. 127, # 15, p. 4591 - 4594,4]
  • 14
  • [ 21298-55-5 ]
  • [ 615-37-2 ]
  • [ 201230-82-2 ]
  • (3-(pyridin-2’-yl)thiophen-2-yl)(o-tolyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
75% With benz<b>oxazole; (η4-1,5-cyclooctadiene)dichlororuthenium(II); potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Autoclave; Inert atmosphere;
  • 15
  • [ 872-31-1 ]
  • C11H20AlNO [ No CAS ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
83% With palladium diacetate; tris-(o-tolyl)phosphine In toluene at 20℃; for 5h; Inert atmosphere;
  • 16
  • [ 21298-55-5 ]
  • [ 10521-96-7 ]
  • (E)-2-(2-styryl-thiophen-3-yl)-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With (η6-1,3,5-cyclooctatriene)(η4-1,5-cyclooctadiene)ruthenium(0) In toluene at 120℃; for 50h; Inert atmosphere;
  • 17
  • [ 21298-55-5 ]
  • [ 615-37-2 ]
  • [ 201230-82-2 ]
  • (3-(pyridin-2’-yl)thiophen-2-yl)(o-tolyl)methanone [ No CAS ]
  • [ 1610886-05-9 ]
YieldReaction ConditionsOperation in experiment
91% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 18
  • [ 21298-55-5 ]
  • [ 201230-82-2 ]
  • [ 2113-51-1 ]
  • [ 1610885-65-8 ]
YieldReaction ConditionsOperation in experiment
72% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 19
  • [ 21298-55-5 ]
  • [ 201230-82-2 ]
  • [ 90-14-2 ]
  • [ 1610885-66-9 ]
YieldReaction ConditionsOperation in experiment
59% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 20
  • [ 21298-55-5 ]
  • [ 4214-28-2 ]
  • [ 201230-82-2 ]
  • [ 1610885-67-0 ]
YieldReaction ConditionsOperation in experiment
41% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 21
  • [ 21298-55-5 ]
  • [ 201230-82-2 ]
  • [ 696-62-8 ]
  • [ 1610885-68-1 ]
YieldReaction ConditionsOperation in experiment
56% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 22
  • [ 21298-55-5 ]
  • [ 352-34-1 ]
  • [ 201230-82-2 ]
  • [ 1610885-69-2 ]
YieldReaction ConditionsOperation in experiment
55% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 23
  • [ 21298-55-5 ]
  • [ 201230-82-2 ]
  • [ 22445-41-6 ]
  • [ 1610885-70-5 ]
YieldReaction ConditionsOperation in experiment
47% With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;
  • 24
  • [ 109-04-6 ]
  • 3-thiophenyl boronic acid [ No CAS ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
97% With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 14h;
  • 25
  • [ 21298-55-5 ]
  • [ 653-34-9 ]
  • [ 201230-82-2 ]
  • [ 1627500-39-3 ]
YieldReaction ConditionsOperation in experiment
74% With dichloro(1,5-cyclooctadiene)ruthenium(II) polymer In water at 20 - 130℃; for 24h; Autoclave; Inert atmosphere; Sealed tube;
  • 26
  • [ 21298-55-5 ]
  • [ 55305-43-6 ]
  • 3-(pyridin-2-yl)thiophene-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bromopentacarbonylmanganese(I); N-cyclohexyl-cyclohexanamine; zinc(II) chloride In 1,4-dioxane at 100℃; for 16h; Schlenk technique; Inert atmosphere;
85% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; sodium acetate In 1,2-dichloro-ethane at 110℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;
  • 27
  • [ 21298-55-5 ]
  • [ 135205-66-2 ]
  • 3-(pyridin-2-yl)thiophene-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere;
  • 28
  • [ 21298-55-5 ]
  • palladium(II) acetate [ No CAS ]
  • [Pd(2,3'-thienylpyridine)(μ-O2CCH3)]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% In dichloromethane for 2h; Reflux; Preparation of [Pd(2,3′-thpy)(μ-O2CCH3)]2, 1a To a solution of 2,3′thpy (0.0717 g, 0.445 mmol) in CH2Cl2 (20mL) was added solid Pd(O2CCH3)2 (0.100 g, 0.445 mmol). The solution was heated at reflux for 2 h, during which time the reaction was monitored using TLC (silica gel, CH2Cl2). The reaction mixture was diluted with CH2Cl2 (40 mL) and washed with water (2×25 mL). The CH2Cl2 was removed under reduced pressure yielding a yellow precipitate. The product was recrystallized with CH2Cl2/hexanes. Yield: 0.101 g, 0.154 mmol, 69%. Anal. Calc. for C22H18N2O4Pd2S2: C, 40.57, H, 2.79, N, 4.30. Found: C, 40.59, H, 2.65, N, 4.22. δH (400MHz, CD2Cl2) (only major isomer peaks reported): 7.76 (d, J=5.04Hz, 1H), 7.44 (m, 1H), 6.88 (d, J=7.79Hz, 1H), 6.80 (d, J=5.04Hz, 1H), 6.74 (d, J=5.04Hz, 1H), 6.49 (t, J=6.18Hz, 1H), 2.20 (s, 17H). δC (101MHz, CD2Cl2) (only major isomer peaks reported): 183.46, 160.75, 153.83, 150.28, 144.22, 138.93, 123.81, 121.73, 119.62, 117.35, 24.31. νmax/cm-1: 3096, 3054, 2986, 2929, 1605, 1563, 1559, 1539, 1531, 1499, 1474, 1412, 1399, 1384, 1354, 1341, 1292, 1282, 1274, 1166, 1154, 1130, 1074, 1050, 1030, 999, 968, 888, 878, 865, 853, 795, 784, 776, 770, 760, 755, 739, 722, 698, 686, 633, 628, 620, 616, 555, 511, 502, 485, 469.
  • 29
  • [ 21298-55-5 ]
  • palladium(II) acetate [ No CAS ]
  • cis-[Pd(2,3'-thienylpyridine)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% In dichloromethane at 20℃; for 120h; Preparation of cis-[Pd(2,3′-thpy)2], 1c To a solution of Pd(O2CCH3)]2 (0.091 g, 0.406 mmol) in CH2Cl2 (10 mL) was added 2,3′thpy (0.131 g, 0.813 mmol). The solution was stirred at rt for 5 d. After 2h, the reaction mixture changed from orange to light yellow. After 3 d, a yellow precipitate appeared. The solid was collected and dried in vacuo. The yellow filtrate was transferred to crystallization tubes for diffusion with Et2O. Yield: 0.063 g, 0.148 mmol, 36%. Anal. Calc. for C18H12N2PdS2*0.25 CH2Cl2: C, 48.92, H, 2.81, N, 6.25. Found: C, 48.98, H, 2.99, N, 6.35. δH (400MHz, CD2Cl2): 8.57 (d, J=5.0Hz, 2H), 7.85 (dd, J=7.4Hz, 2H), 7.59 (d, J=7.8Hz, 2H), 7.43 (J=5.0Hz, 2H), 7.35 (d, J=5.0Hz, 2H), 7.20 (dd, J=6.0Hz, 2H).
  • 30
  • [ 21298-55-5 ]
  • [ 140-10-3 ]
  • (E)-2-(2,4-distyryl-thiophen-3-yl)-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 2,2-dimethylpropanoic anhydride In toluene at 140℃; for 12h; Inert atmosphere;
  • 31
  • [ 21298-55-5 ]
  • [ 140-10-3 ]
  • (E)-2-(2-styryl-thiophen-3-yl)-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 2,2-dimethylpropanoic anhydride In toluene at 140℃; for 24h; Inert atmosphere;
  • 32
  • [ 21298-55-5 ]
  • [ 6773-29-1 ]
  • methyl 5-oxo-5H-thieno[3,2-a]quinolizine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With carbonyl(η-5-cyclopentadienyl)diiodocobalt(III); Ag(1+)*(x)F6Sb; potassium acetate In 2,2,2-trifluoroethanol at 120℃; for 24h; Inert atmosphere; Schlenk technique;
  • 33
  • [ 21298-55-5 ]
  • [ 55305-43-6 ]
  • 3-(pyridin-2-yl)thiophene-2-carbonitrile [ No CAS ]
  • 3-(pyridin-2-yl)thiophene-2,4-dicarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 77% 2: 21% With silver hexafluoroantimonate; carbonyl(η-5-cyclopentadienyl)diiodocobalt(III); potassium acetate In 1,2-dichloro-ethane at 120℃; for 16h; Inert atmosphere; Schlenk technique; chemoselective reaction;
  • 34
  • [ 21298-55-5 ]
  • [ 35466-83-2 ]
  • 2-(2-allylthiophen-3-yl)pyridine [ No CAS ]
  • 2-(2,4-diallylthiophen-3-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 77% 2: 20% With dimanganese decacarbonyl; sodium acetate In 1,4-dioxane at 100℃; for 14h; Schlenk technique; Inert atmosphere;
  • 35
  • [ 21298-55-5 ]
  • [ 1070-19-5 ]
  • N-(tert-butyloxycarbonyl)-2-amino-3-(pyridin-2-yl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate; silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 80℃; for 14h; Inert atmosphere; Schlenk technique;
  • 36
  • [ 21298-55-5 ]
  • Zhdankin’s reagent [ No CAS ]
  • C16H14N2O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate; magnesium oxide In 1,2-dichloro-ethane at 80℃; for 15h; regioselective reaction;
  • 37
  • [ 924-44-7 ]
  • [ 21298-55-5 ]
  • ethyl thieno[3,2-a]indolizine-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; copper diacetate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Sealed tube;
  • 38
  • [ 6165-69-1 ]
  • [ 26838-86-8 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
62% With palladium diacetate; sodium carbonate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 130℃; Inert atmosphere; Schlenk technique;
  • 39
  • [ 21298-55-5 ]
  • [ 1469-70-1 ]
  • 2-(4-allylthiophen-3-yl) pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; potassium carbonate In chlorobenzene at 100℃; for 48h; Inert atmosphere; regioselective reaction;
  • 40
  • [ 21298-55-5 ]
  • [ 1173898-37-7 ]
  • (E)-4-methyl-4-{2-[3-(pyridin-2-yl)thiophen-2-yl]vinyl}-1,3-dioxolan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With bromopentacarbonylmanganese(I); acetic acid In 1,4-dioxane at 100℃; for 0.333333h; Flow reactor; chemoselective reaction;
  • 41
  • [ 21298-55-5 ]
  • [ 392-41-6 ]
  • methyl 2-oxo-2-(thieno[3,2-a]indolizin-9-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; water; sodium acetate In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 42
  • [ 21298-55-5 ]
  • [ 14088-57-4 ]
  • 1-phenyl-3-(3-(pyridin-2-yl)thiophen-2-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With silver tetrafluoroborate; bromopentacarbonylmanganese(I); sodium acetate In 1,2-dimethoxyethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 43
  • [ 21298-55-5 ]
  • [ 14088-57-4 ]
  • 3,3'-(3-(pyridin-2-yl)thiophene-2,4-diyl)bis(1-phenylpropan-1-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With silver tetrafluoroborate; bromopentacarbonylmanganese(I); triphenylborane; sodium acetate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 44
  • [ 50-00-0 ]
  • [ 21298-55-5 ]
  • C10H9NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With bromopentacarbonylmanganese(I); sodium acetate In 1,4-dioxane at 80℃; for 5.5h;
  • 45
  • [ 109-09-1 ]
  • [ 21298-55-5 ]
  • 2,3,4,5-tetra(2-pyridyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(benzene)ruthenium(II) dimer; sodium carbonate; Trimethylacetic acid In 1-methyl-pyrrolidin-2-one at 220℃; for 3h; Microwave irradiation; Inert atmosphere; 11 Synthesis Example 1] (Invention)Synthesis of Exemplified Compound (3) -8 General procedure: In a sample vial for microwave synthesizer manufactured by Biotage, 0.155 g of Exemplified compound (1) -1, 0.908 g of Exemplified compound (2) -1, 20.4 mg of pivalic acid, 0.636 g of sodium carbonate, 5.0 mL of NMP as a solvent and 30.6 mg of [RuCl2 (η6-C6H6)] 2 as a catalyst were added, and after bubbling with nitrogen gas, the cap was capped with a dedicated cap and mounted in a microwave device and heated at 220 ° C. for 1 hour. It was stirred. After the reaction, the reaction mixture was cooled to room temperature, the solvent NMP was distilled off under reduced pressure, and the residue was purified by a silica gel chromatogram to obtain 0.990 g (yield 93%) of a desired compound, Exemplified Compound (3) -8.
  • 46
  • [ 21298-55-5 ]
  • [ 81-07-2 ]
  • C16H10N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; sodium acetate In 2,2,2-trifluoroethanol; acetonitrile at 100℃; for 48h; Inert atmosphere; Sealed tube; 2.3. General procedure for synthesis of product 5 or 6 General procedure: Arenes (1/4, 0.2 mmol), 2 (0.3 mmol), PhI(OAc)2 (0.3mmol), [Cp*RhCl2]2 (4 mol%), NaOAc (0.06 mmol), and TFE(1.0 mL), CH3CN (1.0 mL) were charged into a pressure tube.The reaction mixture was stirred at 100 °C for 48 h. After thesolvent was removed under reduced pressure, the residue waspurified by silica gel chromatography using PE/EA (2:1) toafford compound 5/6.
  • 47
  • [ 21298-55-5 ]
  • [ 14078-85-4 ]
  • C12H19B10NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; copper diacetate; silver trifluoromethanesulfonate; lithium carbonate In toluene at 130℃; for 12h; Sealed tube; Inert atmosphere;
  • 49
  • [ 109-04-6 ]
  • [ 214360-70-0 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
271 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 12h; Inert atmosphere; Sealed tube;
  • 50
  • [ 21298-55-5 ]
  • [ 100-52-7 ]
  • phenyl[3-(pyridin-2-yl)thiophen-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With tert.-butylhydroperoxide; palladium diacetate; Trimethylacetic acid In decane; 1,2-dichloro-ethane at 80℃; for 0.5h; Inert atmosphere; Microwave irradiation; Sealed tube; regioselective reaction;
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