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Chemical Structure| 111359-74-1 Chemical Structure| 111359-74-1

Structure of 111359-74-1

Chemical Structure| 111359-74-1

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Product Details of [ 111359-74-1 ]

CAS No. :111359-74-1
Formula : C12H21NOSi
M.W : 223.39
SMILES Code : NC1=CC=C(O[Si](C)(C(C)(C)C)C)C=C1

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Application In Synthesis of [ 111359-74-1 ]

* 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 [ 111359-74-1 ]

[ 111359-74-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 10386-27-3 ]
  • [ 111359-74-1 ]
  • 2-({4-[(tert-butyldimethylsilyl)oxy]phenyl}amino)pyridine-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos; In toluene; at 50℃; for 1.5h;Inert atmosphere; Preparation 21": 2-({4-[(tert-Butyldimethylsilyl)oxy]phenyl}amino)pyridine-4-carbonitrile A solution composed of <strong>[10386-27-3]2-bromo-4-pyridinecarbonitrile</strong> (5.00 g, 36.1 mmol), 4-[(tert-butyldimethylsilyl)oxy]aniline (8.06 g, 36.1 mmol), sodium tert-butylate (4.50 g, 46.9 mmol) and 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.458 g, 1.08 mmol) in toluene (50 mL) is purged with nitrogen. Tris(dibenzylideneacetone)-dipalladium(0) (0.99 g, 1.08 mmol) is then added to the reaction mixture, and then the batch is heated at 50° C. for 1.5 hours. The mixture is then allowed to cool to ambient temperature. Water is added and the reaction mixture is extracted with ethyl acetate (3*20 mL). The combined organic phases are washed with brine, and then concentrated under reduced pressure. The crude product is absorbed onto silica gel and purified by chromatography over silica gel using ethyl acetate and heptane as eluants. The product obtained is dissolved in the warm state in heptane and precipitates, with stirring, at ambient temperature, and then at 0° C. After filtration, the expected compound is obtained in the form of a solid. 1H NMR (400 MHz, CDC3) delta ppm: 0.22 (s, 6H), 1.00 (s, 9H), 6.61 (br. s, 1H), 6.81-6.84 (m, 2H), 6.84-6.89 (m, 2H), 7.12-7.17 (m, 2H), 8.26 (dd, J=5.1, 0.9 Hz, 1H) 13C NMR (100 MHz, CDC3) delta ppm: -4.29, 18.31, 25.78, 109.11, 114.73, 117.23, 121.17, 121.74, 124.93, 132.12, 149.79, 153.45, 158.00 MS (ESI+): [M+H]+ 326.19
 

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