524695-42-9

Basic information

• Product Name: N-benzyl-4-methyl-N-(14-pyridin-3-yl-tetradec-2-enyl)-benzenesulfonamide
• Synonyms: N-benzyl-4-methyl-N-(14-pyridin-3-yl-tetradec-2-enyl)-benzenesulfonamide
• CAS NO: 524695-42-9
• Molecular Weight: 532.791
• Mol File: 524695-42-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-benzyl-4-methyl-N-(14-pyridin-3-yl-tetradec-2-enyl)-benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-4-methyl-N-(14-pyridin-3-yl-tetradec-2-enyl)-benzenesulfonamide(524695-42-9)
• EPA Substance Registry System: N-benzyl-4-methyl-N-(14-pyridin-3-yl-tetradec-2-enyl)-benzenesulfonamide(524695-42-9)

Safety Data

• Hazardous Substances Data: 524695-42-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1120-90-7 3-iodopyridine 
• 21964-49-8 tetradeca-1,13-diene 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 

Downstream Products

• 524695-43-0 Benzyl-((E)-14-pyridin-3-yl-tetradec-2-enyl)-amine 

Relevant articles and documents

Synthesis of naturally occurring pyridine alkaloids via palladium-catalyzed coupling/migration chemistry

The palladium-catalyzed cross-coupling of 3-iodopyridine, long-chain terminal dienes, and benzylic amines or tosylamides provides a novel route to key intermediates for the synthesis of the naturally occurring, biologically active pyridine alkaloids theonelladins C and D, niphatesine C, and xestamine D. This process involves (1) oxidative addition of the heterocyclic iodide to Pd(0), (2) carbopalladation of the least hindered carbon-carbon double bond of the diene, (3) palladium migration, and (4) π-allylpalladium displacement by the nitrogen nucleophile with simultaneous regeneration of the Pd catalyst. Subsequent hydrogenation and deprotection affords good yields of the natural products. The Pd-catalyzed coupling of 3-iodopyridine and 2-methyl-11-dodecen-1-ol provides a convenient synthesis of a long-chain aldehyde by an analogous palladium migration process, which is easily converted to the pyridine alkaloid ikimine A.