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Chemical Structure| 1029654-18-9 Chemical Structure| 1029654-18-9

Structure of 1029654-18-9

Chemical Structure| 1029654-18-9

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Product Details of [ 1029654-18-9 ]

CAS No. :1029654-18-9
Formula : C7H10BNO2
M.W : 150.97
SMILES Code : CC1=CN=C(C)C(=C1)B(O)O
MDL No. :MFCD07437924

Safety of [ 1029654-18-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 1029654-18-9 ]

* 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 [ 1029654-18-9 ]

[ 1029654-18-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1029654-18-9 ]
  • [ 148231-12-3 ]
  • [ 1197332-58-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; toluene; at 105℃; for 4h;Inert atmosphere; n-BuLi (1.6 M in hexanes, 6.7 ml_, 10.8 mmol, 2.0 equiv) was added dropwise to a cold (- 78C) solution of 3-bromo-2,5-dimethyl-pyridine (Bulletin de Ia Societe Chimique de France, 1972, (6), 2466-81 ) (1 g, 5.38 mmol) in Et2O (20 ml_), under an argon atmosphere. The reaction mixture was stirred for 1 h at -78C. Triisopropyl borate (3.7 ml_, 16.1 mmol, 3.0 equiv) was then added. The reaction mixture was allowed to warm to rt, quenched by addition of a saturated solution of NH4CI (1 ml_), and concentrated. The residue was diluted with EtOAc/H2O and the pH adjusted to 7. The aqueous layer was separated and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated to afford 170 mg of the title compound as a beige solid (batch 1 ). The aqueous layer was concentrated, the residue combined with batch 1 and dissolved in EtOH (5 ml_). This solution was added to a mixture of <strong>[148231-12-3]5,8-dibromo-quinoxaline</strong> (800 mg, 2.8 mmol) (Step 1.5), PdCI2(dppf) (1 13 mg, 0.1 mmol, 0.05 equiv), Na2COs (2 M solution in H2O, 5.6 ml_, 1 1.1 mmol, 4 equiv) in toluene (30 ml.) at 1050C, under an argon atmosphere. The reaction mixture was stirred at 105 0C for 4 h, allowed to cool to rt, diluted with EtOAc and H2O, and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (Hex/EtOAc, 1 :4) to afford 250 mg of the title compound as a purple solid: ES-MS: 314.0 / 316.0 [M+H]+; tR= 2.63 min (System 1 ); Rf = 0.09 (Hex/EtOAc, 1 :4).
 

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