5-Nitroindole → HCID 21202645, compound

HRID 1978921Notes

Reaction equation

HRID 1978921 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].[CH3:15][O:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21]Br>C(#N)C>[CH3:15][O:16][C:17]([CH2:18][CH2:19][CH2:20][CH2:21][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)=[O:23]

Participants

5

Reactant 3

HCID 225235-NitroindoleHCID 24758Sodium hydrideHCID 79557Methyl 5-bromovalerate

Product 1

HCID 21202645HCID 21202645, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 5-nitroindole (0.324 g, 2.0 mmol) in anhydrous acetonitrile (10 ml) was added sodium hydride (0.057 g, 2.38 mmol). The resulting red-brown solution was stirred for 45 minutes, before the addition of a solution of methyl-5-bromovalerate (0.429 g, 2.2 mmol) in anhydrous acetonitrile (1 ml). The solution was stirred for 21 hours, during which time a solid precipitated. Analysis by TLC in chloroform:ethanol (99:1) after 2 hours showed 2 components (starting material: Rf=0.5, 1-(4-methoxycarbonyl butyl)5-nitroindole: Rf=0.8). Further analysis after 21 hours indicated the reaction was essentially complete. The reaction mixture was poured into ethyl acetate (20 ml) and molar HCl (20 ml) and the phases separated. The aqueous phase was extracted with ethyl acetate (20 ml) and the combined organic layer washed with molar sodium bicarbonate solution. The ethyl acetate solution was dried over anhydrous sodium sulphate, filtered and rotary evaporated to give a yellow oil (0.5 g, 1.81 mmol, 91%).

Workup

  1. customprecipitated
  2. waitAnalysis by TLC in chloroform:ethanol (99:1) after 2 hours showed
  3. waitFurther analysis after 21 hours indicated
  4. additionThe reaction mixture was poured into ethyl acetate (20 ml) and molar HCl (20 ml)
  5. customthe phases separated
  6. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  7. washthe combined organic layer washed with molar sodium bicarbonate solution
  8. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customrotary evaporated

Sources & evidence

ORD record
ord-2b96bb2ba2654585a2876a387cbf0637
Source dataset
uspto-grants-2001_05
Patent number
US06239159B1

Reaction notes

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