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Chemical Structure| 346-43-0 Chemical Structure| 346-43-0

Structure of 346-43-0

Chemical Structure| 346-43-0

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Product Details of [ 346-43-0 ]

CAS No. :346-43-0
Formula : C11H10FNO5
M.W : 255.20
SMILES Code : O=C(OCC)C(CC1=CC=C(F)C=C1[N+]([O-])=O)=O
MDL No. :MFCD17019381

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* 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 [ 346-43-0 ]

[ 346-43-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 346-43-0 ]
  • [ 348-37-8 ]
YieldReaction ConditionsOperation in experiment
81% With iron; In ethanol; acetic acid; for 3.5h;Heating / reflux; (3-2) Ethyl 3-(4-fluoro-2-nitrophenyl)-2-oxopropanoate (5.51 g, 21.6 mmol) obtained in Reference Example (3-1) was dissolved in a mixed solvent of ethanol-acetic acid (1:1, 84 ml), and iron powder (10.9 g, 144 mmol) was added thereto, followed by heating under reflux for 3.5 hours. After the reaction mixture was diluted with tetrahydrofuran, the insolubles were filtered through Celite, and the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (elution solvent: methylene chloride/acetone=15/1) to obtain ethyl 6-fluoro-1H-indole-2-carboxylate (3.62 g, yield: 81%). 1H-NMR (400MHz, CDCl3): delta 8.89 (1H, br. s), 7.61 (1H, dd, J = 8.8, 5.5 Hz), 7.20 (1H, m), 7.09 (1H, dd, J = 9.4, 2.0 Hz), 6.94 (1H, ddd, J = 9.4, 8.8, 2.0 Hz), 4.41 (2H, q, J = 7.0 Hz), 1.42 (3H, t, J = 7.0 Hz).; (9-6) Ethyl 3-(4-fluoro-2-nitrophenyl)-2-oxopropanoate (5.51 g, 21.6 mmol) obtained in Reference Example (9-5) was dissolved in a mixed solvent of ethanol-acetic acid (1:1, 84 ml), and iron powder (10.9 g, 144 mmol) was added thereto, followed by heating under reflux of the mixture for 3.5 hours. The temperature of the reaction mixture was returned to room temperature, and the mixture was diluted with tetrahydrofuran. The insolubles were removed by filtration using Celite, and the filtrate was concentrated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (elution solvent: methylene chloride/acetone=15/1) to obtain ethyl 6-fluoro-1H-indole-2-carboxylate as yellow crystals (3.62 g, yield: 81%). 1H-NMR (400MHz, CDCl3) : delta 8.89 (1H, br. s), 7.61 (1H, dd, J = 8.8, 5.5 Hz), 7.20 (1H, m), 7.09 (1H, dd, J = 9.4, 2.0 Hz), 6.94 (1H, ddd, J = 9.4, 8.8, 2.0 Hz), 4.41 (2H, q, J = 7.0 Hz), 1.42 (3H, t, J = 7.0 Hz).
 

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