380227-43-0

Basic information

• Product Name: 3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide
• Synonyms: 3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide
• CAS NO: 380227-43-0
• Molecular Weight: 384.802
• Mol File: 380227-43-0.mol

Chemical Properties

• CAS DataBase Reference: 3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide(380227-43-0)
• EPA Substance Registry System: 3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide(380227-43-0)

Safety Data

• Hazardous Substances Data: 380227-43-0(Hazardous Substances Data)

Upstream product

• 13959-02-9 3-bromoisonicotinic acid 
• 122365-23-5 N-[(diphenylphosphinoyl)methyl]-N-methylamine 
• 88912-27-0 3-chloro-isonicotinic acid 

Downstream Products

• 380227-39-4 (E)-3-(2-iodobenzylidene)-2-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one 
• 73335-60-1 2-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one 
• 200411-10-5 3-diphenylphosphinoyl-2-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one 

Relevant articles and documents

A short and efficient synthesis of 3-diphenylphosphoryl- and 3-diethoxyphosphoryl(aza)isoindolinones: Extension to the sulfonylated analogs

A variety of 3-diphenylphosphoryl- and 3-diethoxyphosphoryl(aza)isoindolinones have been efficiently prepared by aryne- and hetaryne-mediated cyclization of phosphorylated α-amino carbanions derived from suitably substituted 2- and 3-halobenzamide and 3-chloropyridine-4-carboxamide derivatives. The synthesis of some 3-sulfonylated analogs by extension of this principle has been achieved.

A concise total synthesis of the azaphenanthrene alkaloid eupolauramine

A six-step total synthesis of the azaphenanthrene alkaloid eupolauramine 1 has been achieved using combinational metalation-cyclization tactics. The synthetic route involved first the construction of the azaisoindolinone 9 by aryne-mediated cyclization of he phosphorylated pyridocarboxamide 7 and subsequent dephosphorylation. Metalation of 9 followed by connection of the hydroxybenzyl appendage and E1CB anti-elimination allowed the formation of the halogenoarylmethylene azaisoindolinone 4 in the exclusive E-form. Oxidative radical cyclization gave rise to the azaphenanthrene skeleton and regioselective bromination of 3 induced the incorporation of the bromine atom at the 6-position of the azaphenanthrene lactam. Ultimate replacement of the bromine atom of 2 by the methoxy functionality by sequential transmetalation, in situ oxidation, and O-methylation of the phenolic derivative 14 completed the synthesis of the target natural product eupolauramine.