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Chemical Structure| 864972-21-4 Chemical Structure| 864972-21-4

Structure of 864972-21-4

Chemical Structure| 864972-21-4

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Product Details of [ 864972-21-4 ]

CAS No. :864972-21-4
Formula : C23H26FN3O4
M.W : 427.47
SMILES Code : O=C([C@]12CC3=C(N(C4=CC=C(F)C=C4)N=C3)C=C1CCN(C(OC(C)(C)C)=O)C2)OC

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Application In Synthesis of [ 864972-21-4 ]

* 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 [ 864972-21-4 ]

[ 864972-21-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 864972-21-4 ]
  • [ 175205-81-9 ]
  • tert-butyl (4aR)-1-(4-fluorophenyl)-4a-(4-(trifluoromethyl)-picolinoyl)-4a,5,7,8-tetrahydro-1H-pyrazolo[3,4-g]-isoquinoline-6(4H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.65 g A solution of <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (2344 nil, 18.95 mmol) in dry ether (15 mL) was added drop wise over 15 minutes to a solution of isopropylmagnesium chloride (2M, 9.47 mi, 18.95 mmol) in dry ether (30 mL) at 0 °C, during which the solution darkened to a brown colour. After stirring at 0 °C for a further 45 minutes a solution of (R)-6-tert-butyl 4a- methyl l -(4-fluorophenyl.)-4a,5,7,8-tetrahydro-l H-pyrazolo[3,4-g]isoquinoline-4a,6(4H)- diearboxylate (2.7 g, 6.32 mmol) in dry ethentetrahydrofuran (4: 1 , 30 mL total) was added dropwise over 20 minutes at 0 °C. The resulting dark coloured solution was stirred at 0 °C for 20 minutes, then stirred at room temperature for a further 2 hours. The reaction mixture was diluted with ice/water (20 mL), acidified with I M HCl (40 mL) and extracted with ethyl acetate (100 mL). The organic phase was washed sequentially with water (50 mL), saturated sodium hydrogen carbonate solution (50 mL) and brine (30 mL), dried (magnesium sulphate), filtered and evaporated in vacuo to give a brown gum. This was dissolved in acetonitrile (50 mL), I M HCl (10 mL) was added, a d the solution stirred for 2 hours at room temperature. Ethyl acetate (150mL) was added and the organic phase washed sequentially with brine (30 mL), saturated aqueous sodium hydrogen carbonate (50 mL) ami further brine (30 mL). The organic phase was then dried (magnesium sulphate), filtered and evaporated in vacuo. [0251] The residual brown gum was purified twice by column chromatography on silica gel (gradients: 0-10percent ethyl acetate in dichloromethane, and 0-30percent ethyl acetate in isohexane) to give (R)-tert-butyl 1 -(4-fluorophenyl)-4a-(4-(trif3.uoromethyl)picolinoyl)-4a,5,7,8-tetrahydro-l H- pyrazolo[3,4-g]isoquinoiine-6(4H)-carboxylate (2.65 g) as a light brown foam. LCMS (Method F, ES-API): RT 2.91 min, m+H = 543.
 

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