2-Methyl-2-butene → 6-chloro-1H-indole-2,3-dicarboxylic acid 2-ethyl ester

HRID 1865982Notes

Reaction equation

HRID 1865982 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:15]=[O:16])=[CH:12][CH:11]=[C:10]([Cl:17])[CH:9]=2)=[O:5])[CH3:2].CC(=CC)C.[O-:23]Cl=O.[Na+]>CC(O)(C)C>[CH3:2][CH2:1][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]([OH:23])=[O:16])=[CH:12][CH:11]=[C:10]([Cl:17])[CH:9]=2)=[O:5]

Participants

5

Reactant 3

HCID 105532-Methyl-2-buteneHCID 4591751Ethyl 6-chloro-3-formyl-1H-indole-2-carboxylateHCID 23668197Sodium Chlorite

Product 1

HCID 451210676-chloro-1H-indole-2,3-dicarboxylic acid 2-ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of commercially available 6-chloro-3-formyl-1H-indole-2-carboxylic acid ethyl ester in t-BuOH and 2-methyl-2-butene (50 eq) was added 9.2 eq NaClO2 (9 eq) and aq. NaH2PO4 (7 eq) and stirred 12 h at room temperature. After concentration the mixture was dissolved in H2O and adjusted to pH7 and then extracted with EtOAc; partial concentration of the organic phase precipitated the product in 52% yield.

Workup

  1. concentrationAfter concentration the mixture
  2. dissolutionwas dissolved in H2O
  3. extractionextracted with EtOAc
  4. concentrationpartial concentration of the organic phase
  5. customprecipitated the product in 52% yield

Sources & evidence

ORD record
ord-5c4041b248b44d62b71b8117abe321cf
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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