Pyruvic Acid → 6-Chloro-1H-indole-2-carboxylic acid

HRID 1466910Notes

Reaction equation

HRID 1466910 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[C:10]([OH:15])(=[O:14])[C:11]([CH3:13])=O.C1N2CCN(CC2)C1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([CH:13]=[C:11]([C:10]([OH:15])=[O:14])[NH:7]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 6396975-Chloro-2-iodoaniline

Product 1

HCID 855846-Chloro-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-Chloro-2-iodoaniline (5.8 g, 23 mmol) and pyruvic acid (8 mL, 115 mmol) were dissolved in DMF (100 mL). DABCO (12.8 g, 115 mmol) was added and N2 (g) was bubbled through solution for 20 minutes, then palladium acetate (1.03 g, 4.6 mmol) was added. The reaction was heated to 110° C. for 1 hour then submitted to aqueous workup and purified by silica gel chromatography (0-100% EtOAc in hexanes) to yield the title compound.

Workup

  1. customN2 (g) was bubbled through solution for 20 minutes
  2. custompurified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3c37bce5ab274f138cbbbc2e7c60824b
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

Loading…