Methyl iodide → 1-(1-Methyl-1H-indol-5-yl)ethanone

HRID 10633Notes

Reaction equation

HRID 10633 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.IC.[C:15](=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 407321-(1H-indol-5-yl)ethan-1-one

Product 1

HCID 122962601-(1-Methyl-1H-indol-5-yl)ethanoneYield 51.5%

Procedure

Ex-28A: To a solution of 1-(1H-indol-5-yl)-ethanone (Yang, Y. et al, Heterocycles, 1992, 34(6), 1169–1175; 0.45 g, 2.8 mmol) were added iodomethane (3 mL) and cesium carbonate (2.3 g, 7.1 mmol). The reaction mixture was allowed to stir at 55° C. for 1.5 day during which additional iodomethane (11 mL) was added. The reaction was quenched with water. The aqueous solution was extracted with ether. The solution of ether was washed with saturated solution sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (33%, v/v, in hexane) gave 1-(1-methyl-1H-indol-5-yl)-ethanone (0.25 g, 51%). 1H NMR (CDCl3) δ 8.30 (s, 1H), 7.91 (dd, J=1.2, 8.1 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.12 (d, J=3.2 Hz, 1H), 6.61 (d, J=3.0, 1H), 3.82 (s, 3H), 2.66 (s, 3H).

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionThe aqueous solution was extracted with ether
  4. washThe solution of ether was washed with saturated solution sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washElution with ethyl acetate (33%, v/v, in hexane)

Sources & evidence

ORD record
ord-9ccfd343f2824477a48c1ff905b1543b
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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