2-Methyl-2-butene → 1-Benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic Acid

HRID 40065Notes

Reaction equation

HRID 40065 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:25]=[O:26])=[C:11]([CH:22]([CH3:24])[CH3:23])[N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].CC(=CC)C.[O-:32]Cl=O.[Na+]>CC(O)(C)C.CC#N.O>[CH2:15]([N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:14]=2)[C:10]([C:25]([OH:32])=[O:26])=[C:11]1[CH:22]([CH3:23])[CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 59762439Ethyl1-Benzyl-3-formyl-2-isopropyl-1H-indole-6-carboxylate2×

Product 1

HCID 597623601-Benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

General Procedure D. To a solution of ethyl1-benzyl-3-formyl-2-isopropyl-1H-indole-6-carboxylate (Compound 35, 220 mg, 0.63 mmol) in t-BuOH (6 ml), CH3CN (1 ml), and 2-methyl-2-butene (1.76 ml) was added a solution of NaH2PO4 (1.51 g, 12.6 mmol) and NaClO2 (80%, 1.13 g, 12.6 mmol) in H2O (6 ml). The mixture was stirred at room temperature fro 12 h. 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→20% EtOAc-hexanes) to yield the title compound as a yellow solid.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (×3)
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-6a624b21890b48aca288f53503223b7e
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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