2-Methyl-2-butene → 6-Methoxy-2-(methoxycarbonyl)-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxylic Acid

HRID 40099Notes

Reaction equation

HRID 40099 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:7]2[C:12]([C:13]=1[CH:14]=[O:15])=[CH:11][CH:10]=[C:9]([O:16][CH3:17])[CH:8]=2)=[O:4].CC(=CC)C.[O-:30]Cl=O.[Na+]>CC(O)(C)C.O1CCOCC1.O>[CH3:17][O:16][C:9]1[CH:8]=[C:7]2[C:12]([C:13]([C:14]([OH:30])=[O:15])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 59762382Methyl3-Formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate2×

Product 1

HCID 597623576-Methoxy-2-(methoxycarbonyl)-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxylic Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

General Procedure K. To a suspension of methyl3-formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate (Compound 91, 1.64 g, 5.07 mmol) in t-BuOH (120 ml) and dioxane (20 ml) was added 2-methyl-2-butene (25 ml) and a solution of NaH2PO4 (7.3 g, 61 mmol) and NaClO2 (80%, 5.7 g, 50.7 mmol) in H2O (100 ml). The reaction was stirred at room temperature for 6 h, extracted with EtOAc (×2). 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→100% EtOAc-hexanes) to yield the title compound as an off-white solid.

Workup

  1. extractionextracted with EtOAc (×2)
  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→100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a90ae63450c6419eacbacb57289ecc8c
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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