Methyl 3-amino-4-(2,6-dichlorophenylethynyl)-benzoate → methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate

HRID 1514935Notes

Reaction equation

HRID 1514935 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[C:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])[C:5]([O:7][CH3:8])=[O:6]>C(#N)C.C(#N)C.C(#N)C.[Pd](Cl)Cl>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]1[NH:1][C:2]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2

Participants

4

Reactant 1

HCID 66966063Methyl 3-amino-4-(2,6-dichlorophenylethynyl)-benzoate

Product 1

HCID 66965661methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 3-amino-4-(2,6-dichlorophenylethynyl)-benzoate (450 mg, 1.41 mmol) and palladium (II) chloride bis(acetonitrile) (90 mg, 347 μmol) in acetonitrile (5 mL) was heated at 65° C. for 2 h. The solvent was removed on under reduced pressure and the residue was purified by chromatography using a gradient of 10-30% heptane/ethyl acetate to give methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate.

Workup

  1. customThe solvent was removed on under reduced pressure
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-69cb15b654d64a5b926ea9d6754c205c
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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