2-Methyl-2-butene → 1-Benzyl-2-isopropyl-6-methoxy-1H-indole-3-carboxylic Acid

HRID 40033Notes

Reaction equation

HRID 40033 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH:19]=[O:20])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.[OH:29]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+]>CC(O)(C)C.CC#N.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([C:19]([OH:29])=[O:20])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-butene2×HCID 516951Monobasic potassium phosphate2×HCID 23668197Sodium Chlorite2×HCID 597623941-Benzyl-2-isopropyl-6-methoxy-1H-indole-3-carbaldehyde2×

Product 1

HCID 597623541-Benzyl-2-isopropyl-6-methoxy-1H-indole-3-carboxylic Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 1-benzyl-2-isopropyl-6-methoxy-1H-indole-3-carbaldehyde (Compound 5, 608 mg, 1.98 mmol) in t-BuOH (15 ml), CH3CN (15 ml), and 2-methyl-2-butene (10 ml) was added a solution of KH2PO4 (5.4 g, 39.6 mmol) and NaClO2 (80%, 4.5 g, 39.6 mmol) in H2O (50 ml). The mixture was stirred at room temperature and additional 2-methyl-2-butene, KH2PO4, and NaClO2 were added at the above ratio every 16-24 h until the starting material was consumed. The reaction mixture was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes) to yield the title compound as a yellow solid.

Workup

  1. customwas consumed
  2. extractionThe reaction mixture was extracted with EtOAc (×3)
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-df34ff595be44ca7a2a241a02c99ab6e
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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