Dimethylformamide → Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

HRID 907110Notes

Reaction equation

HRID 907110 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].O=P(Cl)(Cl)Cl.[OH-].[Na+].CN([CH:26]=[O:27])C>>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:26]=[O:27])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22467242HCID 22467242, compound

Product 1

HCID 59425156Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylateYield 96%

Procedure

1-Ethyl-1H-indole-6-carboxylic acid methyl ester (900 mg, 4.45 mmol) was dissolved in DMF (3.3 mL). This was added dropwise to an ice-cold solution of POCl3 (430 μL, 4.5 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was then treated with 6N NaOH (3.5 ml). The mixture was then partitioned between H2O and ethyl acetate. Purification by silica gel chromatography (5-10% EtOAc/CH2Cl2) yielded 1-ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (985 mg, 96%) as a white solid.

Workup

  1. customThe mixture was then partitioned between H2O and ethyl acetate
  2. customPurification by silica gel chromatography (5-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-c2e7a986b1c9473396136c293937256e
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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