Pyruvic Acid → 5-(methoxycarbonyl)-1H-indole-2-carboxylic acid

HRID 459998Notes

Reaction equation

HRID 459998 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6](I)[CH:5]=1.O=[C:14]([CH3:18])[C:15]([OH:17])=[O:16].N12CCN(CC1)CC2>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][C:14]([C:15]([OH:17])=[O:16])=[CH:18]2)=[O:12]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 529879165-(methoxycarbonyl)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 25 g 4-Amino-3-Iodo-benzoic acid methyl ester, 19 ml 2-Oxo-propionic acid, 30.4 g 1,4-Diaza-bicyclo[2.2.2]octane and 1 g Pd(OAc)2 in 200 ml DMF was heated under argon to 100° C. After 5 h the reaction mixture was concentrated under reduced pressure and the residue was partitioned between 300 ml ethyl acetate and 200 ml 1 M hydrochloric acid. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to yield a yellow solid (6.4 g). From the aqueous layer additional product slowly precipitated as a white solid (7.9 g) which was collected by filtration. Both fractions were combined, dried in vacuo and used in the next reaction without further purification. Yield: 14.3 g. MS (ES+): m/e=220.

Workup

  1. concentrationAfter 5 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between 300 ml ethyl acetate and 200 ml 1 M hydrochloric acid
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-35919f35e89f46fca4e139c71b46f740
Source dataset
uspto-grants-2007_03
Patent number
US07196103B2

Reaction notes

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