1-Fluoro-3-nitrobenzene → Ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate

HRID 565044Notes

Reaction equation

HRID 565044 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

Participants

5

Reactant 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 21194451HCID 21194451, compound

Product 1

HCID 21194305Ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylateYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 0.50 g (1.97 mmol) of ethyl 4-chloro-7-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.16 g (3.94 mmol) of 60% sodium hydride and 10 ml of dimethylformamide, the suspension was stirred at room temperature for 30 minutes. Then 0.28 g (1.9.7 mmol) of 1-fluoro-3-nitrobenzene was added to the solution at room temperature followed by stirring for 3 hours at 150° C. After cooling, the reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 0.18 g (24.3%) of ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate.

Workup

  1. stirringby stirring for 3 hours at 150° C
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto ice water
  4. extractionThe resulting mixture was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was isolated
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-01eee370c8dd454cbcfb4fcd222051cb
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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