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Chemical Structure| 1071454-96-0 Chemical Structure| 1071454-96-0

Structure of 1071454-96-0

Chemical Structure| 1071454-96-0

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Product Details of [ 1071454-96-0 ]

CAS No. :1071454-96-0
Formula : C21H33BN2O4Si
M.W : 416.39
SMILES Code : CC(C1=CN(COCC[Si](C)(C)C)C2=NC=C(B3OC(C)(C)C(C)(C)O3)C=C21)=O
MDL No. :MFCD13195035

Safety of [ 1071454-96-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 1071454-96-0 ]

* 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 [ 1071454-96-0 ]

[ 1071454-96-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 866545-96-2 ]
  • [ 76513-69-4 ]
  • [ 73183-34-3 ]
  • [ 1071454-96-0 ]
YieldReaction ConditionsOperation in experiment
92% To a 250 ml 3-neck flask, <strong>[866545-96-2]1-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-ethanone</strong> (2.2 g, 9.3 mmol) and DMF (50 ml) were added. The solution was cool to -40 C. under nitrogen, and sodium hydride (0.3 g, 11.2 mmol) was added in 2 batches. The mixture was stirred at -40 C. for 1 hour. A solution of SEM-Cl (2 ml, 11.2 mmol) in DMF (10 ml) was added dropwise and the resulting mixture was allowed to stir at -40 C. for another 2 hours. The reaction was quenched with saturated NH4Cl (40 ml) and worked up with ethyl acetate, brine, dried with Na2SO4 and concentrated to dryness. The crude intermediate, bis(pinacolato)diboron (4.8 g, 18.6 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (341 mg, 0.5 mmol), and sodium acetate (2.3 g, 28 mmol) in DMF (20 ml) were stirred at 100 C. overnight. The mixture was allowed to cool to room temperature and was then extracted with ethyl acetate (3×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 1-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl-1-2(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine-3-yl)-ethanone (3.6 g, 92% yield). 1H NMR (500 MHz, DMSO-d6) delta 0.03 (s, 9H), 0.92 (m, 2H), 1.28 (s, 3H), 1.43 (s, 12H), 3.67 (m, 2H), 5.78 (s, 2H), 8.68, (m, 1H), 8.82 (s, 1H), 8.89 (m, 1H). MS: m/z 417.2 (M+H+).
 

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