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Chemical Structure| 323580-68-3 Chemical Structure| 323580-68-3

Structure of 323580-68-3

Chemical Structure| 323580-68-3

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Product Details of [ 323580-68-3 ]

CAS No. :323580-68-3
Formula : C13H14ClNO2
M.W : 251.71
SMILES Code : O=C(N1C=CC2=C1C=C(Cl)C=C2)OC(C)(C)C
MDL No. :MFCD08689510

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Application In Synthesis of [ 323580-68-3 ]

* 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 [ 323580-68-3 ]

[ 323580-68-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 323580-68-3 ]
  • [ 352359-22-9 ]
YieldReaction ConditionsOperation in experiment
To a solution of 6-chloro-indole-l -carboxylic acid tert-butyl ester (2 g) in dry THF (10 mL) is added triisopropyl borate (2.74 mL) under N2. The mixture is cooled to O0C in an ice bath. Lithium diisopropylamine (4.97 mL, 2 M) is added over an hour at 0C. The reaction is stirred at O0C for 30 minutes. 2 N HCl (IO mL) is added. The resulting mixture is extracted with EtOAc. The organic layer is dried, filtered and concentrate. The residue is purified by flash chromatography on silica gel eluting with 5% to 60% EtOAc in heptane to afford 1 -ffert-butoxycarbonyD--chloro- 1 H-indol-2- ylboronic acid as a solid (1 g).
  • 2
  • [ 323580-68-3 ]
  • [ 80041-89-0 ]
  • tert-butyl 6-isopropyl-1H-indole-1-carboxylate [ No CAS ]
  • 3
  • [ 323580-68-3 ]
  • [ 5419-55-6 ]
  • [ 7732-18-5 ]
  • [ 352359-22-9 ]
YieldReaction ConditionsOperation in experiment
91.5% To 16 g of N-Boc-6-chloroindole, 71 g of tetrahydrofuran and 17.9 g of triisopropyl borate was added, Cooled to 5 C and the LDA solution was added dropwise to the solution, After completion of the dropwise addition, the reaction was stirred for 20 minutes. (LDA solution was added dropwise from 33.3 ml of 2.5 mol/L n-butyllithium 9.1g diisopropylamine and 35.5 g of tetrahydrofuran mixed solution prepared) The reaction solution was added dropwise to 120 g of a dilute aqueous hydrochloric acid solution, And the aqueous layer was extracted with 30 g of methyl tert-butyl ether; The organic phases were combined and washed with 21 g of saturated brine, Dried over 4 g of anhydrous sodium sulfate, filtered and concentrated; After adding 16 g of n-heptane, the mixture was concentrated under reduced pressure. The concentrated residue was slurried with 16.3 g of n-heptane, filtered, dried, To give a yellow solid (N-Boc-6-chloro-1H-indol-2-yl)boronic acid 17.2g, HPLC purity 98.0%, yield 91.5%.
 

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