916574-87-3

Usage

Core structure

1H-Pyrrolo[2,3-b]pyridine

Methoxy group

Contains a single oxygen atom bonded to a methyl group

Phenylsulfonyl group

Consists of a phenyl ring attached to a sulfonyl group, which is a functional group containing a sulfur atom bonded to two oxygen atoms

Usage

Commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds

Potential applications

Medicinal chemistry and drug discovery

Unique features

Unique structure and reactivity

InChI:InChI=1/C14H12N2O3S/c1-19-13-7-9-15-14-12(13)8-10-16(14)20(17,18)11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 122379-63-9 4-methoxy-1H-pyrrolo<2,3-b>pyridine 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 1085278-87-0 4-methoxy-2-methyl-1-(phenylsulfonyl)pyrrolo[2,3-b]pyridine 

Relevant academic research and scientific papers

Painting argyrins blue: Negishi cross-coupling for synthesis of deep-blue tryptophan analogue β-(1-azulenyl)-L alanine and its incorporation into argyrin C

The argyrins are a family of non-ribosomal peptides that exhibits different biological activities through only small structural changes. Ideally, a biologically active molecule can be tracked and observed in a variety of biological and clinical settings in a non-invasive manner. As a step towards this goal, we report here a chemical synthesis of unnatural deep blue amino acid β-(1-azulenyl)-L alanine with different fluorescence and photophysical properties, which allows a spectral separation from the native tryptophan signal. This might be especially useful for cell localization studies and visualizing the targeted proteins. In particular, the synthesis of β-(1-azulenyl)-L alanine was achieved through a Negishi coupling which proved to be a powerful tool for the synthesis of unnatural tryptophan analogs. Upon β-(1-azulenyl)-L alanine incorporation into argyrin C, deep blue octapeptide variant was spectrally and structurally characterized.

Application of selective palladium-mediated functionalization of the pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine heterocyclic system for the total synthesis of variolin B and deoxyvariolin B

The reaction of protected 3-bromo-2-(bromomethyl)-4-methoxypyrrolo[2,3-b] pyridine and tosylmethyl isocyanide (TosMIC) afforded a pyrido[3′, 2′:4,5]pyrrolo[1,2-c]pyrimidine derivative in good yield. This compound was transformed through installation of the pyrimidine moiety in the C5 position, hydrolysis, and decarboxylation in an advanced intermediate for the total or formal synthesis of the naturalalkaloid variolin B. Reaction of 3-bromo-2-(bromomethyl)-4-chloropyrrolo[2,3-b]pyridine with N-tosylmethyl dichloroformimide as a synthetic TosMIC equivalent afforded trihalo-substituted pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine. This compound was used in a new total synthesis of the alkaloid variolin B by selective and sequential C-N, C-C, and C-O palladium-mediated functionalization at the C9, C5, and C4 positions of the pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine system. A formal synthesis of deoxyvariolin B is also described by using the same synthetic strategy. A new synthesis for deoxyvariolin B and the natural product variolin B was achieved by selective and sequential palladium-mediated functionalization of di- or trihalo-substituted pyrido[3′,2′:4,5] pyrrolo[1,2-c]pyrimidine.