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Chemical Structure| 136818-43-4 Chemical Structure| 136818-43-4

Structure of 136818-43-4

Chemical Structure| 136818-43-4

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Product Details of [ 136818-43-4 ]

CAS No. :136818-43-4
Formula : C10H8FNO2
M.W : 193.17
SMILES Code : O=C(C(N1)=CC2=C1C=C(F)C=C2)OC
MDL No. :MFCD04966976

Safety of [ 136818-43-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 136818-43-4 ]

* 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 [ 136818-43-4 ]

[ 136818-43-4 ] Synthesis Path-Downstream   1~2

  • 1
  • potassium 2-(4-fluoro-2-nitrophenyl)-1-methoxy-carbonylethenolate [ No CAS ]
  • potassium 2-(4-fluoro-2-nitrophenyl)-1-ethoxycarbonylethenolate [ No CAS ]
  • [ 348-37-8 ]
  • [ 136818-43-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; iron; In ethanol; water; at 0℃; for 5h;Heating / reflux; 1.2. Methyl 6-fluoro-1H-indole-2-carboxylate A mixture of 35 g of potassium salt obtained in stage 1.1. in 500 ml of ethanol is cooled to approximately 0 C. 80 ml of concentrated hydrochloric acid are added in small portions. 35 g (627 mmol) of iron powder are also added portionwise. The mixture is heated at reflux for 5 h and then cooled and filtered. The solid obtained is rinsed with dichloromethane. The filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel with a mixture of solvents (dichloromethane/ethyl acetate: 100/0 to 70/30). The chromatography fractions are partially concentrated. The solid which precipitates is collected by filtration, washed with cyclohexane and dried under reduced pressure. 18 g of a white solid formed of methyl 6-fluoro-1H-indole-2-carboxylate are obtained, comprising 10 to 20% of ethyl 6-fluoro-1H-indole-2-carboxylate.
  • 2
  • [ 348-37-8 ]
  • [ 136818-43-4 ]
  • [ 74-88-4 ]
  • [ 550349-31-0 ]
  • [ 550349-32-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1 Compound 1 7-fluoro-N,N,5-trimethyl-4-oxo-3-(pyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide 1.1. Methyl 6-fluoro-1-methyl-1H-indole-2-carboxylate A 60% suspension of 7.9 g (197 mmol) of sodium hydride (washed with petroleum ether beforehand) and 36.1 g (176 mmol) of m<strong>[348-37-8]ethyl 6-fluoro-1H-indole-2-carboxylate</strong> (containing 10 to 20% of <strong>[348-37-8]ethyl 6-fluoro-1H-indole-2-carboxylate</strong>) in 250 ml of N,N-dimethylformamide is stirred at ambient temperature for 2 h. Then 12 ml (193 mmol) of iodomethane in 50 ml of N,N-dimethylformamide are added and the mixture is stirred at ambient temperature for 12 h. The contents are poured into an ice/water mixture. Dichloromethane is added and the aqueous phase is neutralized with hydrochloric acid (1N). The organic phase is separated off, washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a silica gel column in a mixture of solvents (cyclohexane/dichloromethane: 50/50 to 0/100 then dichloromethane/ethyl acetate: 100/0 to 70/30). 32.7 g (170 mmol) are isolated of a white compound of methyl 6-fluoro-1-methyl-1H-indole-2-carboxylate containing 10 to 20% of ethyl 6-fluoro-1-methyl-1H-indole-2-carboxylate.
 

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