HCID 22627179, compound → HCID 22627286, compound

HRID 1108686Notes

Reaction equation

HRID 1108686 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-6e0686bc4eba4edbb4776acada098bbb
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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