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Chemical Structure| 20357-37-3 Chemical Structure| 20357-37-3

Structure of 20357-37-3

Chemical Structure| 20357-37-3

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Product Details of [ 20357-37-3 ]

CAS No. :20357-37-3
Formula : C19H15Cl2NO3
M.W : 376.23
SMILES Code : O=C(Cl)CC1=C(C)N(C(C2=CC=C(Cl)C=C2)=O)C3=C1C=C(OC)C=C3

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Application In Synthesis of [ 20357-37-3 ]

* 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 [ 20357-37-3 ]

[ 20357-37-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 104594-70-9 ]
  • [ 20357-37-3 ]
  • 3-[3,4-bis[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyloxy]phenyl]-(2E)-2-propenoic acid 2-phenylethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
449 mg With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 22℃; for 4h;Inert atmosphere; Fig. 3 shows the synthesis of VP964. A solution of thionyl chloride (0.203ml, 2.80mmol) in 1.5ml of anhydrous toluene was slowly added to a solution of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid (indomethacin, Sigma Aldrich, Italy, 500mg, 1.40mmol) in 6ml of anhydrous toluene cooled at 0C and under nitrogen atmosphere. The mixture was then stirred under nitrogen, for 4h, at reflux. After this period, toluene was removed and the obtained mixture was used in the subsequent step without any further purification. A solution of CAPE (180mg, 0.635mmol) and N,N-diisopropylethylamine (0.44ml, 2.54mmol) in 6ml of anhydrous THF was added drop-wise to crude 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride dissolved in anhydrous THF (2ml) and the mixture was stirred under nitrogen for 4h at 22C. After removing the THF, the mixture was dissolved in ethyl acetate. The obtained organic phase was washed with water (2×75ml) followed by saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated. The isolated crude material was purified by column chromatography (silica gel 60, 230-400mesh, Merck) using ethyl acetate/cyclohexane (3:7) as eluant. The title compound was obtained as white solid (449mg, 74%): mp 80-81C; IR (KBr) cm-1 3424, 2933, 1769, 1685, 1594, 1478, 1359, 1319, 1242, 1112, 835, and 752; 1H NMR (DMSO-d6) delta 7.74-7.55 (s, 10H+1H, aromatic+CH=CHCOO), 7.37-7.16 (m, 6H, aromatic), 7.11-7.05 (m, 2H, aromatic), 6.97-6.88 (m, 2H, aromatic), 6.77-6.71 (m, 2H, aromatic), 6.61 (d, J=16.0, 1H, CH=CHCOO), 4.36 (t, J=6.8Hz, 2H, OCH2CH2Ph), 3.92 (s, 2H+2H, CH2COO+CH2COO), 3.70 (s, 3H+3H, OCH3+OCH3), 2.96 (t, J=6.8Hz, 2H, OCH2CH2Ph), 2.20 (s, 3H, CH3). 2.17 (s, 3H, CH3). Anal. (C55H44Cl2N2O10) C, H, N.
 

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