177274-70-3

Upstream product

• 584-08-7 potassium carbonate 
• 177274-68-9 N-((3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl)methyl)benzenesulfonamide 
• 107-05-1 3-chloroprop-1-ene 
• 98-10-2 benzenesulfonamide 
• 85678-41-7 N-benzenesulphonyl-2-methyl-3-thiophenoxyindole 
• 106-95-6 allyl bromide 
• 98-09-9 benzenesulfonyl chloride 
• 1496-78-2 3-bromo-2-methyl-1H-indole 
• 177274-67-8 3-bromo-2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole 
• 177274-66-7 1-phenylsulfonyl-3-bromo-2-methylindole 

Relevant academic research and scientific papers

Synthesis of 4-substituted-1,2,3,4-tetrahydro-β-carbolines via intramolecular radical cyclisation and Heck reaction

A convenient method for the synthesis of 4-substituted-β-carbolines from the corresponding N-allylisogramine derivative is reported using intramolecular free radical cyclisation or Heck reaction.

Pd(0)-Catalyzed Intramolecular Heck reaction of 2/3-Aryl(amino)methyl-3/2-bromoindoles: Syntheses of 3,4-Benzo[ c]-β-carbolines, Benzo[4,5]isothiazolo[2,3- a]indole 5,5-Dioxides, and 1,2-Benzo[ a]-γ-carbolines

One-pot synthesis of 3,4-benzo[c]-β-carbolines was achieved from 2-aryl(tosylamino)methyl-3-bromoindoles via 10 mol % Pd(OAc)2/PPh3-mediated intramolecular Heck coupling using K2CO3 as a base in DMF at 110 °C with concomitant aromatization through an elimination of tosylsulfinic acid. Under identical conditions, the isomeric 3-aryl(tosylamino)methyl-2-bromoindoles upon intramolecular Heck reaction furnished benzo[4,5]isothiazolo[2,3-a]indole 5,5-dioxides instead of the expected γ-carbolines. However, synthesis of the expected γ-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-γ-carbolines, could be achieved from 3-aryl(tosylamino)methyl-2-bromoindoles containing a mesitylene sulfonyl unit as a protecting group on the indole nitrogen.