186504-53-0

Basic information

• Product Name: PdCl(C₈H₄N(CH₃)CH₂N(CH₃)2)(P(C₆H₅)3)
• CAS NO: 186504-53-0
• Molecular Weight: 591.428
• Mol File: 186504-53-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: PdCl(C₈H₄N(CH₃)CH₂N(CH₃)2)(P(C₆H₅)3)(CAS DataBase Reference)
• NIST Chemistry Reference: PdCl(C₈H₄N(CH₃)CH₂N(CH₃)2)(P(C₆H₅)3)(186504-53-0)
• EPA Substance Registry System: PdCl(C₈H₄N(CH₃)CH₂N(CH₃)2)(P(C₆H₅)3)(186504-53-0)

Safety Data

• Hazardous Substances Data: 186504-53-0(Hazardous Substances Data)

Upstream product

• 52972-61-9 3-(N,N-dimethylaminomethyl)-1-methylindole 
• 186504-44-9 di-μ-chloro-[1-methyl-2-((3-dimethylamino)methyl)-1H-indolyl-C(2),N]dipalladium(II) 
• 603-35-0 triphenylphosphine 

Relevant articles and documents

Cyclometallation of indole derivatives: Cyclopalladation of gramine and 1-methyl gramme and CO insertion

Li2PdCl4, in methanol, with gramine 1 and 1-methyl gramine 2 gave the dimeric complexes 1a and 2a with chlorine bridges and having the indole nucleus metallated at position 2. The corresponding bromo derivatives 1b and 2b were isolated from the reactions of Pd(OAc)2 with 1 and 2, followed by treatment with LiBr. Complexes 1a,b and 2a,b gave the monomeric, cyclometallated derivatives 3a-d by reaction with PPh3 in methylene chloride. When the cyclopalladation of 1-methyl gramine 1 was attempted by reacting PdCl2, PPh3 and 2 in methanol in the presence of AcONa, an unexpected compound 4 was obtained. A structural determination of 4 showed it consisted of the known [Pd(PPh3)Cl3]- anion packed with the dimethyl-bis(3-methylene-1-methyl indole) ammonium cation. When compounds 1a and 2a were reacted with carbon monoxide at atmospheric pressure in methanol or ethanol and in the presence of NEt3, the corresponding 2-carboalkoxy indole derivatives 5 and 6 were isolated in high yields.