HCID 22627179, compound → HCID 22627286, compound

HRID 278072Notes

Reaction equation

HRID 278072 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=O)[CH:2]([CH3:4])[CH3:3]>O1CCCC1>[CH2:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 22627179HCID 22627179, compound

Product 1

HCID 22627286HCID 22627286, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-isobutyrylindole-6-carboxylate (146 mg) in tetrahydrofuran (5 ml) was added 1M solution of brane-tetrahydrofuran complex in tetrahydrofuran (1.8 ml), and the mixture was stirred at 50° C. for 1 hour. The resulting mixture was evaporated in vacuo, and the residue was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, and dried over sodium sulfate. After evaporation of solvent, the residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (2:1) to give methyl 3-isobutylindole-6-carboxylate (105 mg) as colorless crystals.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was quenched with aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of solvent
  7. customthe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-ed93b2f20ee14de288ce143bd28fa34f
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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