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Chemical Structure| 2510-23-8 Chemical Structure| 2510-23-8
Chemical Structure| 2510-23-8

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Product Citations

Product Citations

Krzysztof Kuciński ; Grzegorz Hreczycho ;

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C−H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

Alternative Products

Product Details of 3-Ethynylpyridine

CAS No. :2510-23-8
Formula : C7H5N
M.W : 103.12
SMILES Code : C#CC1=CC=CN=C1
MDL No. :MFCD02177459
InChI Key :CLRPXACRDTXENY-UHFFFAOYSA-N
Pubchem ID :186003

Safety of 3-Ethynylpyridine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H315-H319
Precautionary Statements:P210-P240-P241-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Class:4.1
UN#:1325
Packing Group:

Application In Synthesis of 3-Ethynylpyridine

* 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 [ 2510-23-8 ]

[ 2510-23-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 2510-23-8 ]
  • [ 145691-59-4 ]
  • [ 752224-60-5 ]
  • 3
  • [ 216393-67-8 ]
  • [ 2510-23-8 ]
  • [ 1202551-89-0 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; for 1h;Reflux; To a mixture of 3-ethynylpyridine (1.13 g, 11 mmol) and 2-fluoro^-chloro-6-iodoaniline (2.71 g, 10 mmol) in triethylamine (100 mL) is added PdCI2(PPh3)2 (175 mg, 0.25 mmol) and CuI (95 mg, 0.50 mmol) and the mixture is refluxed for 1 h. The solvent is removed in vacuo and the residue is purified by silica gel flash chromatography (dichloromethane- methanol, 1 :0 to 24:1 ) to give 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine. MS (ESI) m/z 247 (M+H)+.
  • 4
  • [ 2510-23-8 ]
  • [ 5572-94-1 ]
  • [ 1244016-73-6 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 60℃; for 2h;Inert atmosphere; B. 3-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)pyridine; In an oven dried round bottom flask, a solution of <strong>[5572-94-1]2-(4-iodophenyl)-5,5-dimethyl-1,3,2-dioxaborinane</strong> (21 g, 66.47 mmol) and triethylamine (27.8 mL, 199.40 mmol) in acetonitrile (305 mL) was degassed with a stream of N2 for 5 minutes. After this time, 3- ethynylpyridine (7.20 g, 69.79 mmol), Pd(PPh3)2Cl2 (3.5 g, 4.99 mmol) and copper(I) iodide (0.633 g, 3.32 mmol) were added. The flask was then placed in a 60 0C oil bath and was stirred for 2 h, until TLC indicated formation of a new product. The reaction was allowed to cool to room temperature and was then concentrated in vacuo. The resulting brown solid was dissolved in DCM and then impregnated on silica gel. The crude material was purified by silica gel chromatography (5-50% Ethyl Acetate in Hexanes) to afford the desired product as a yellow solid (16.2 g, 83%). 1U NMR (300 MHz, DMSO-d6) δ: ppm 8.77 (s, IH); 8.61 (d, IH); 7.98 (d, IH); 7.76 (d, 2H); 7.58 (d, 2H); 7.48 (dd, IH), 3.78 (s, 4H); 0.97 (s, 6H).
  • 5
  • [ 2510-23-8 ]
  • [ 160893-07-2 ]
  • [ 1423778-41-9 ]
YieldReaction ConditionsOperation in experiment
57% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 80℃; for 24h;Inert atmosphere; General procedure: To a solution of 2-chloroquinoline (29.7 mg, 0.182 mmole) in THF (1.5 mL) was added PdCl2(PPh3)2 (2.6 mg, 0.0037 mmole), CuI (1.5 mg, 0.0063 mmol). The reaction mixture was stirred for 5 min and triethylamine (0.15 mL) and phenylacetylene (0.03 mL, 0.27 mmol) were added. After the resulting mixture was stirred at 80 C for 24 h, it was allowed to cool to room temperature and filtered through a pad of Celite by the aid of EtOAc. The filtrate was treated with water and extracted with EtOAc (3 x 10 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/hexane = 1:10) to give 2-(phenylethynyl)quinoline 5a (25 mg, 60%)
  • 6
  • [ 2510-23-8 ]
  • [ 4181-20-8 ]
  • N,N-bis(4-iodophenyl)-4'-(3-pyridylethynyl)phenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.6% In a 50 mL three-neck round bottom flask equipped with magnetic stirrer, condenser and nitrogen inlet-outlet were introduced3-ethynylpyridine (0.165 g, 1.6 mmol), PdCl2*2PPh3 (0.056 g,0.08 mmol), CuI (0.03 g, 0.16 mmol), PPh3 (0.04 g, 0.16 mmol), triethylamine (15 mL) and tetrahydrofuran (5 mL). The mixture was stirred in nitrogen atmosphere at 50-60 °C for an hour after that 4,4',4''-trisiodotriphenylamine (1 g, 1.6 mmol) dissolved in a mixture of TEA (5 mL) and THF (5 mL) was added. Then the mixture was stirred at 80 °C when the solution color turned out in time from yellow to red and some solids are deposited on the flask's walls. After 24 h the mixture was precipitated in water, filtrated and dried. The pure orange compound 3 was obtained by silica gel chromatography using ethyl acetate/hexane (1:4 vol/vol) as eluent.Yield: 46.6percent. Mp 80 °C. ESI-MS 599.2 (M H). IR (KBr, cm-1): 3032, 2212, 1647, 1599, 1575, 1504, 1479, 1404, 1314, 1284, 1265, 1179, 1142, 1001, 818, 803, 700. 1H NMR (CDCl3, ppm): 8.75 (1H,pyridyl), 8.54 (1H, d, H, pyridyl), 7.81 (1H, d, pyridyl, J 8.0 Hz), 7.57(4H, d, J 8.8 Hz), 7.41 (2H, d, J 8.4 Hz), 7.28 (1H, t, pyridyl), 7.01(2H, d, J 8.4 Hz), 6.85 (4H, d, J 8.8 Hz).
  • 7
  • [ 2510-23-8 ]
  • [ 827-08-7 ]
  • 3-[(2-bromo-3,4,5,6-tetrafluorophenyl)ethynyl]pyridine [ No CAS ]
 

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