Water → 1-(2,2-Dimethylpropyl)-1H-indole-3-carboxylic acid

HRID 1393666Notes

Reaction equation

HRID 1393666 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[H-].[Na+].[CH2:15](I)[C:16]([CH3:19])([CH3:18])[CH3:17].O>CN(C)C=O>[CH3:15][C:16]([CH3:19])([CH3:18])[CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69867Indole-3-Carboxylic AcidHCID 84953Propane, 1-iodo-2,2-dimethyl-

Product 1

HCID 230920031-(2,2-Dimethylpropyl)-1H-indole-3-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Indole-3-carboxylic acid (208 mg) was dissolved in N,N-dimethylformamide (10 ml), then sodium hydride (154 mg) was added thereto, and the mixture was stirred for 10 minutes at room temperature. Neopentyl iodide (0.25 ml) was added to the reaction solution and stirred for 15 hours at 80° C. Water was added to the reaction mixture which was then washed with ethyl acetate. The aqueous phase was adjusted to pH 6 by 1 N hydrochloric acid, extracted with ethylacetate, and the extract was washed with a saturated saline solution and dried over sodium sulfate anhydrous. The resulting product was concentrated under reduced pressure, and the residue was purified by column chromatography (eluting solvent; n-hexane:ethyl acetate 4:1) to give the title compound (264 mg, Y.:89%).

Workup

  1. stirringstirred for 15 hours at 80° C
  2. washwas then washed with ethyl acetate
  3. extractionextracted with ethylacetate
  4. washthe extract was washed with a saturated saline solution
  5. dry with materialdried over sodium sulfate anhydrous
  6. concentrationThe resulting product was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography (eluting solvent; n-hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-0891ebc6531c443985f2b4fe4968f646
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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