Methyl iodide → 6-Bromo-1-methylindole-2-carbaldehyde

HRID 2365417Notes

Reaction equation

HRID 2365417 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH:13]=[O:14])[NH:10]2)=[CH:6][CH:5]=1.[CH3:15]I>CN(C=O)C>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH:13]=[O:14])[N:10]2[CH3:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135679586-Bromo-1H-indole-2-carbaldehyde

Product 1

HCID 751762556-Bromo-1-methylindole-2-carbaldehydeYield 106.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% weight dispersion in mineral oil, 80.0 mg, 1.98 mmol) was added to a solution of 6-bromo-1H-indole-2-carbaldehyde (371 mg, 1.66 mmol) in DMF (10.0 mL) at 0° C. under N2. Methyl iodide (0.124 mL, 1.98 mmol) was added, and the reaction mixture was allowed to warm slowly to room temperature. After stirring for 4 h, the mixture was quenched with H2O at 0° C., upon which a solid precipitated out of solution. The slurry was extracted with ethyl ether (3×). The combined organic layers was dried over Na2SO4, filtered and concentrated to give the title compound (422 mg, 99%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.89 (s, 1H), 7.59 (d, J=9.0 Hz, 2H), 7.28 (dd, J=8.5, 2.0 Hz, 1H), 7.22 (s, 1H), 4.07 (s, 3H).

Workup

  1. customthe mixture was quenched with H2O at 0° C., upon which a solid
  2. customprecipitated out of solution
  3. extractionThe slurry was extracted with ethyl ether (3×)
  4. dry with materialThe combined organic layers was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9da60273a6ef4a378b4f0206c49edf14
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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