Dimethylformamide → HCID 45094683, compound

HRID 502133Notes

Reaction equation

HRID 502133 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:22]=[O:23])C>>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH:22]=[O:23])=[CH:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 59425473HCID 59425473, compound

Product 1

HCID 45094683HCID 45094683, compoundYield 81%

Procedure

1-Ethyl-6-methoxy-1H-indole (900 mg, 5.14 mmol) is dissolved in DMF (1.5 mL). This is added dropwise to an ice-cold solution of POCl3 (500 μL, 5.2 mmol) in DMF (1.75 ml). After stirring at room temperature for 90 minutes, the reaction mixture is re-cooled in an ice bath and is slowly quenched with 6N NaOH (4 mL). The reaction mixture is partitioned between EtOAc and H2O. Purification by silica gel chromatography (EtOAc/CH2Cl2, 5/95) yields 1-ethyl-6-methoxy-1H-indole-3-carbaldehyde (849 mg, 81%) as a yellow solid.

Workup

  1. temperaturethe reaction mixture is re-cooled in an ice bath
  2. customis slowly quenched with 6N NaOH (4 mL)
  3. customThe reaction mixture is partitioned between EtOAc and H2O
  4. customPurification by silica gel chromatography (EtOAc/CH2Cl2, 5/95)

Sources & evidence

ORD record
ord-3c5df0f2b57946ad9c349184fa5de27b
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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