Dimethyl Sulfate → 1-methyl-1H-indole-7-carbaldehyde

HRID 215925Notes

Reaction equation

HRID 215925 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1.[CH3:12]OS(OC)(=O)=O.[H-].[Na+]>CN(C=O)C>[CH3:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 110409791-methyl-1H-indole-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1H-indole-7-carbaldehyde (500 mg, 3.444 mmol) and dimethylsulfate (478 mg, 3.789 mmol) in DMF (3 ml) was cannulated into a suspension of NaH (99 mg, 95% in mineral oil, 4.133 mmol) in DMF (2 ml) at 0° C. The reaction was stirred and allowed to warmed up to room temperature for 1 hour. The reaction was quenched with water and the product was extracted with EtOAC (×2). The organic layers were combined and washed with water, and brine, and dried (MgSO4) and the solution was concentrated to produce a light pink solid, which was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe product was extracted with EtOAC (×2)
  3. washwashed with water, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationthe solution was concentrated
  6. customto produce a light pink solid, which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6274e65efd684335a87e423bcb24230c
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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