HCID 54183315, compound → 1-(1,1-Dimethylethyl) 1H-indole-1,6-dicarboxylate

HRID 1533772Notes

Reaction equation

HRID 1533772 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)=O.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54183315HCID 54183315, compound

Product 1

HCID 223445021-(1,1-Dimethylethyl) 1H-indole-1,6-dicarboxylateYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

To a solution of benzyl 1-tert-butoxycarbonylindole-6-carboxylate (450 mg) in 5.0% formic acid-methanol (10.0 ml) was added 10% palladium on carbon (153 mg) and the mixture was stirred under nitrogen atmosphere at ambient temperature for 4 hours. The resulting solution was filtered through a bed of celite and the filtrate was concentrated in vacuo. The residue was diluted with chloroform and the solution was washed successively with water and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with ether:n-hexane (1:5) to give 1-tert-butoxycarbonylindole-6-caroxylic acid (302 mg).

Workup

  1. filtrationThe resulting solution was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with chloroform
  4. washthe solution was washed successively with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ether:n-hexane (1:5)

Sources & evidence

ORD record
ord-d8378e76b8364f3ea86f650aec42a021
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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