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Chemical Structure| 1453798-46-3 Chemical Structure| 1453798-46-3

Structure of 1453798-46-3

Chemical Structure| 1453798-46-3

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Product Details of [ 1453798-46-3 ]

CAS No. :1453798-46-3
Formula : C11H8ClNO
M.W : 205.64
SMILES Code : CC(C1=C2N=C(Cl)C=CC2=CC=C1)=O

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Application In Synthesis of [ 1453798-46-3 ]

* 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 [ 1453798-46-3 ]

[ 1453798-46-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1453798-46-3 ]
  • [ 50607-30-2 ]
  • [ 1453792-26-1 ]
YieldReaction ConditionsOperation in experiment
40% To a solution of l -(2-chloroquinolin-8-yl)ethanone (3.25 g, 15.80 mmol) in 3 mL DCM at 0 °C was added Et3N (2.86 ml, 20.55 mmol) followed by TBSOTf (3.99 ml, 17.38 mmol), dropwise. The reaction was stirred for 1 h, and then was partitioned between saturated aq. NaHCC and DCM. The aq. layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous Na2S04, filtered, and concentrated in vacuo to give 5.71 g of an orange oil. This oil was taken up in 70 mL THF, treated with water (4.56 ml, 253 mmol) and NBS (2.95 g, 16.59 mmol), and stirred at 25 °C for 15 min. The reaction was then partitioned between water and Et20. The organic layer was sequentially washed with saturated aq. NaHC03, water, and saturated aq. NaCl, and the organics layer was dried over anhydrous MgS04, filtered, and concentrated in vacuo to give 6 g of a yellow solid. This solid was treated with NH4OAc (4.87 g, 63.2 mmol) and <strong>[50607-30-2]piperidine-2,4-dione</strong> (see J. Med. Chem. 2008, 51, 487-501 ; 2.145 g, 18.97 mmol) and 70 mL EtOH and stirred at RT for 5 min. The resulting yellow slurry was placed in a sealed vial and heated at 50 °C for 4 h, then cooled and concentrated in vacuo. The residue was partitioned between saturated aq. NaHC03 and DCM. The aq. layer was extracted with DCM (4x), and the combined organics were dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography using 0- 65 percent 90/10 DCM/MeOH in DCM. The product-containing fractions were concentrated to afford 2- (2-chloroquinolin-8-yl)-6,7-dihydro-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (1.86 g, 6.25 mmol, 40 percent yield) as a orange solid: H NMR (400 MHz, DMSO-d6) delta ppm 1 1.71 (1 H, br. s), 8.49 (1 H, d, J=8.6 Hz), 8.09 (1 H, dd, J=7.4, 1.4 Hz), 7.87 - 7.92 (1 H, m), 7.63 - 7.72 (2 H, m), 7.26 (1 H, d, J=2.3 Hz), 6.97 - 7.04 (1 H, m), 3.40 - 3.47 (2 H, m), 2.91 (2 H, t, J=6.9 Hz), m/z (ESI, +ve) 298.0 (M+H)+
 

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