Water → Ethyl 5-nitro-1-propyl-1H-indole-2-carboxylate

HRID 1824972Notes

Reaction equation

HRID 1824972 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].[CH2:20](I)[CH2:21][CH3:22].O>CS(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][CH2:21][CH3:22])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 12068604Ethyl 5-nitro-1-propyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Under argon, 937 mg (4.00 mmol) of ethyl 5-nitro-1H-indole-2-carboxylate (A. Guy, J. -P. Guetté, Synthesis 1980, 222–223) are initially charged in 12 ml of dimethyl sulphoxide. 4.40 mmol of sodium hydride (176 mg of a 60% dispersion in paraffin) are added a little at a time, and the mixture is stirred at 50° C. for 30 min. After cooling to RT, 170 mg (4.40 mmol) of propyl iodide are added, and the mixture is stirred at RT for another 3 h. The reaction mixture is poured into 30 ml of water and extracted with ethyl acetate (6×30 ml). The combined organic phases are washed with 50 ml of sat. sodium chloride sol., dried over sodium sulphate and freed from the solvent using a rotary evaporator. The resulting brown crude product is purified by column chromatography (silica gel 60, mobile phase gradient cyclohexane→cyclohexane-ethyl acetate 3:1), giving the product as second fraction.

Workup

  1. customGuetté, Synthesis 1980, 222–223)
  2. temperatureAfter cooling to RT
  3. stirringthe mixture is stirred at RT for another 3 h
  4. extractionextracted with ethyl acetate (6×30 ml)
  5. washThe combined organic phases are washed with 50 ml of sat. sodium chloride sol.
  6. dry with materialdried over sodium sulphate
  7. customa rotary evaporator
  8. customThe resulting brown crude product is purified by column chromatography (silica gel 60, mobile phase gradient cyclohexane→cyclohexane-ethyl acetate 3:1)
  9. customgiving the product as second fraction

Sources & evidence

ORD record
ord-0b831c1e24f942dbb2cf14fccfc0f1d7
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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