Potassium Iodide → HCID 66898716, compound

HRID 2369853Notes

Reaction equation

HRID 2369853 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:13])=[O:11])[CH:3]=[CH:2]1.[H-].[Na+].[I-].[K+].Br[CH2:19][CH:20]([O:23][CH3:24])[O:21][CH3:22]>CN(C=O)C>[CH3:22][O:21][CH:20]([O:23][CH3:24])[CH2:19][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:13])=[O:11])[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 676694Methyl indole-7-carboxylate

Product 1

HCID 66898716HCID 66898716, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To methyl 1H-indole-7-carboxylate (2.0 g, 11.4 mmol) dissolved in DMF (10 ml) was added sodium hydride (800 mg, 20 mmol) in portions. The mixture was stirred at room temperature for 1 h, then potassium iodide (160 mg, 0.9 mmol) and 2-bromo-1,1-dimethoxyethane (3.4 ml, 28.5 mmol) were added. The mixture was heated to 80° C. and stirred overnight. After cooling to room temperature, the mixture was quenched by saturated aqueous ammonium chloride, extracted with ethyl acetate (3×), washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate) to afford methyl 1-(2,2-dimethoxyethyl)-1H-indole-7-carboxylate (1.77 g, 59%) as a semitransparent liquid: 1H NMR (500 MHz, CDCl3) δ 7.77 (dd, J=4.5, 1.0 Hz, 1H), 7.66 (dd, J=4.3, 1.0 Hz, 1H), 7.19 (d, J=1.5 Hz, 1H), 7.10 (t, J=8.0 Hz, 1H), 6.57 (d, J=1.8 Hz, 1H), 4.54-4.52 (dd, J=5.0, 4.5 Hz, 1H), 4.48 (d, J=2.5 Hz, 2H), 3.96 (s, 3H), 3.31 (s, 6H).

Workup

  1. temperatureThe mixture was heated to 80° C.
  2. stirringstirred overnight
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was quenched by saturated aqueous ammonium chloride
  5. extractionextracted with ethyl acetate (3×)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-46d121c038744db4a8ed092d79ab759e
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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