Indole → HCID 21838287, compound

HRID 1740302Notes

Reaction equation

HRID 1740302 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[C:7]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[Na].N1C2C(=CC=CC=2)C=[CH:24]1.CI>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:24][N:3]1[C:11]2[C:6](=[C:7]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

8

Reactant 5

HCID 798IndoleHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5360545Sodium2×HCID 21838243HCID 21838243, compound

Product 1

HCID 21838287HCID 21838287, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium hydride (0.20 g) in anhydrous toluene (23 ml) was added a hot solution of methyl 3-(indol-4-yl)benzoate (1.16 g) in toluene (5.8 ml). Since a sodium salt did not form, N,N-dimethylformamide (0.5 ml) was introduced. An evolution of gas occurred with the formation of the orange sodium salt of the indole. After being stirred for 20 minutes methyl iodide was added thereto and the mixture was stirred at 60° C. for four hours. Then the sodium iodide was filtered off and washed with toluene. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and acetone (20:1) to afford methyl 3-(1-methylindol-4-yl)benzoate (0.35 g).

Workup

  1. additionwas introduced
  2. additionwas added
  3. filtrationThen the sodium iodide was filtered off
  4. washwashed with toluene
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and acetone (20:1)

Sources & evidence

ORD record
ord-c6d43e39c1dd4f968ddfd40af0751afb
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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