Potassium Iodide → methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

HRID 922437Notes

Reaction equation

HRID 922437 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:15][CH2:16][CH2:17][O:18][CH3:19].[I-].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 5245511-Bromo-3-methoxypropaneHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylateYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl 1H-indole-6-carboxylate (5.0 g) in N,N-dimethylformamide (40 mL) was added dropwise a solution of 1-bromo-3-methoxypropane (5.24 g) in N,N-dimethylformamide (10 mL) under ice-cooling, and then thereto was added potassium iodide (948 mg), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was sequentially added ethyl acetate and water under ice-cooling, and the organic layer was separated. The organic layer was washed with water twice and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1) to give methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate [REx(6-1)] (5.8 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water twice
  5. dry with materialsaturated saline, dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1)

Sources & evidence

ORD record
ord-c7a6004ce3b0481282c49eff9bdd8cb4
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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