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Chemical Structure| 943320-60-3 Chemical Structure| 943320-60-3

Structure of 943320-60-3

Chemical Structure| 943320-60-3

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Product Details of [ 943320-60-3 ]

CAS No. :943320-60-3
Formula : C11H13N3Si
M.W : 215.33
SMILES Code : C[Si](C#CC1=CN=C2C=CC=NN21)(C)C

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Application In Synthesis of [ 943320-60-3 ]

* 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 [ 943320-60-3 ]

[ 943320-60-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 18087-73-5 ]
  • [ 1066-54-2 ]
  • [ 943320-60-3 ]
YieldReaction ConditionsOperation in experiment
81.8% With trans-bis(triphenylphosphine)palladium dichloride; N-cyclohexyl-cyclohexanamine; In acetonitrile; at 80℃; for 1h;Inert atmosphere; Synthesis of compound 10 (0053) <strong>[18087-73-5]3-bromoimidazo[1,2-b]pyridazine</strong> (compound 9: 10 g, 0.05 mol) was dissolved in acetonitrile (100 ml), under protection of nitrogen, trans-dichlorobis(triphenylphosphine)palladium(II) (1.0 g, 1.4 mmol), cuprous iodide (0.3 g, 1.4 mmol), and dicyclohexylamine (11 ml, 0.06 mol) were added, rise the temperature to 80 C, then trimethylsilyl acetylene (8 ml, 0.6 mol) was added slowly into reaction solution, react for 1 hour, detect with TLC, cool down the reaction solution to room temperature, filter the solution, wash the solid with dichloromethane (200 ml), collect the organic phase, evaporate the solvent, add the residue into dichloromethane (100 ml), wash the organic phase with saturated sodium chloride solution (20 ml x2), dry with anhydrous sodium sulfate, evaporate the solvent for the product. Crystallize the product with ethyl acetate/petroleum ether, to give the black powder solid(compound 10:8.9 g, 81.8% yield). (0054) 1HNMR (CDCl3, 400 MHz) delta: 8.47 (dd, J=1.6, 4.4 Hz, 1H), 7.99(s, 1H), 7.96 (dd, J=1.6, 9.2 Hz, 1H), 7.10 (dd, J=4.4, 9.2 Hz, 1H), 0.33 (s, 9H).
71% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; 3-bromoimidazo [1,2-b] pyridazine (36.64 g, 0.186 mol), Pd (pph3) 4 (10.73 g, 9.29 mmol),CuI (5.30g, 0.028mmol) and DIPEA (32.4mL, 0.279mol)Add to N, N dimethylformamide (150mL), under nitrogen protection,Trimethylsilylacetylene (21.89g, 0.223mol) was added, and the reaction was carried out at room temperature for 1h.Pour the reaction solution into 200mL of water,Ethyl acetate extraction (100mL × 3), the organic phase was separated and dried over anhydrous sodium sulfate.filter,After concentration, silica gel column chromatography gave 28.22 g of product with a yield of 71%.
71% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; Add 3-bromoimidazo [1,2-b] pyridazine (36.64g, 0.186mol),Tetrakis (triphenylphosphonium) palladium (10.73g, 9.29mmol),cuprous Iodide(5.30g, 0.028mmol) and N, N-diisopropylethylamine (32.4mL, 0.279mol) were added to N, N-dimethylformamide (150mL), under the protection of nitrogen,Trimethylsilyl acetylene (21.89 g, 0.223 mol) was added by injection, and the reaction was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was poured into 200 mL of water, and the organic phase was extracted with ethyl acetate (100 mL × 3). After drying with sodium, filtering, and concentrating, the product was isolated by column chromatography on silica gel to obtain 28.22 g, with a yield of 71%.
With copper(l) iodide; N-ethyl-N,N-diisopropylamine;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 20℃; for 1h;Sonogashira coupling; A mixture of 3- bromoimidazo[1 ,2-b]pyridazine (36.78 g, 0.186 mol; prepared according to Stanovnik, B. et a/.Synthesis (1981), 12, 987-989), ethynyltrimethylsilane (21.89 g, 0.223 mol), Pd(PPh3)4 (10.73 g, 9.29 mmol), CuI (5.30 g, 0.028 mol), and diisopropylethylamine (32.4 mL, 0.279 mol) in 150 mL of DMF was stirred at ambient temperature, under an atmosphere of N2, for 1 h. The reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 0-5% MeOH/DCM) to provide 28.46 g of product.
28.46 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; 3-((Trimethyisilyl)ethynyl)imidazo[1,2-bJpyridazine: A mixture of 3 -bromoimidazo[ 1,2- b]pyridazine (36.78 g, 0.186 mol; prepared according to Stanovnik, B. eta. Synthesis (1981), 12,987-989), ethynyltrimethylsilane (21.89 g, 0.223 mol), Pd(PPh3)4 (10.73 g, 9.29 mmol), Cu (5.30 g, 0.028 mol), and diisopropylethylamine (32.4 mL, 0.279 mol) in 150 mL of DMF was stirred at ambient temperature, under an atmosphere of N2, for I h. The reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 0-5% MeOH/DCM) to provide 28.46 g of product.
28.46 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; A mixture of <strong>[18087-73-5]3-bromoimidazo[1,2-b]pyridazine</strong> (IIb) (36.78 g, 0.186 mol), ethynyltrimethylsilane (21.89 g, 0.223 mol), Pd(PPh3)4 (10.73 g, 9.29 mmol), CuI (5.30 g, 0.028 mol), and diisopropylethylamine (32.4 mL, 0.279 mol) in 150 mL of DMF was stirred at ambient temperature, under an atmosphere of N2, for 1 hour. The reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 0-5% MeOH/DCM) to provide 28.46 g of 3-((trimethylsilyl)ethynyl)imidazo[1,2-b]pyridazine (IIc).

  • 2
  • [ 7486-35-3 ]
  • [ 18087-73-5 ]
  • [ 943320-60-3 ]
YieldReaction ConditionsOperation in experiment
71% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; Under nitrogen protection,Add to 500 ml eggplant bottle3-bromoimidazo [1,2-b] pyridazine (36.78 g, 0.186 moles)Seoul),Trimethyl ethynylsilane (21.89 g, 0.223 mol)Tetrakis (triphenylphosphine) palladium (10.73 g, 9.29 mmol)Cuprous iodide (5.30 g, 0.028 mol),Diisopropylethylamine (32.4 mL,0.279 mol) and N, N-dimethylformamide150 ml The reaction was stirred at room temperature for 1 hour,The reaction solution was washed with 200 ml of ethyl acetate,200 ml of saturated brine extraction,The organic phase was separated and dried over anhydrous sodium sulfate,filter,The product was chromatographed on a column packed with silica gel to give 28.46 g of product. Yield: 71%
 

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