Sodium hydride → 1H-Indole-5-carboxylic acid, 1-(2-methoxyethyl)-, methyl ester

HRID 2170849Notes

Reaction equation

HRID 2170849 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH3:20]>O>[CH3:20][O:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 671694841H-Indole-5-carboxylic acid, 1-(2-methoxyethyl)-, methyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 1H-indole-5-carboxylate (200 mg, 1.14 mmol) and sodium hydride (60% in oil, 39 mg, 1.71 mmol) in N,N-dimethylformanide (3 mL) was added 1-bromo-2-methoxyethane (190 mg, 1.37 mmol) at room temperature. Then the mixture was stirred at 60° C. for 2 hours. The mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic layer was washed with water (20 mL) and dried over sodium sulfate. After removal of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1) to give 132 mg (50%) of the title compound as colorless syrup.

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe organic layer was washed with water (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-6cb6d67f4d0b4e939f6ee6e390536e4f
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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