290333-01-6

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy-
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy-;4-Methoxy-7-azaindole-2-carbaldehyde
• CAS NO: 290333-01-6
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.18
• Mol File: 290333-01-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.347g/cm³
• Refractive Index: 1.691
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy-(290333-01-6)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy-(290333-01-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37
• Hazardous Substances Data: 290333-01-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

InChI:InChI=1/C9H8N2O2/c1-13-8-2-3-10-9-7(8)4-6(5-12)11-9/h2-5H,1H3,(H,10,11)

Upstream product

• 290332-99-9 2-hydroxymethyl-4-methoxypyrrolo[2,3-b]pyridine 
• 290332-97-7 2-ethoxycarbonyl-4-methoxypyrrolo[2,3-b]pyridine 
• 290332-96-6 ethyl α-azido-β-(4-methoxypyrid-3-yl)acrylate 
• 82257-15-6 4-methoxynicotinaldehyde 
• 620-08-6 4-methoxypyridine 

Downstream Products

• 492438-78-5 9-benzylamino-5-bromo-4-methoxy-6,7-dihydropyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-82-1 5-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-80-9 5-acetyl-9-benzylamino-4-methoxy-6,7-dihydropyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-89-8 [5-(2-Amino-pyrimidin-4-yl)-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-yl]-benzyl-amine 
• 492439-03-9 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol 

Relevant articles and documents

Carbodiimide-mediated preparation of the tricyclic pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine ring system and its application to the synthesis of the potent antitumoral marine alkaloid variolin B and analog

A total synthesis of the marine alkaloid variolin B has been completed in 13 steps in an overall yield of 6.5% from 3-formyl-4-methoxypyridine. Our approach is based on the sequential formation of the 7-azaindole ring, the tricyclic pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine ring system, and finally installation of the 2-aminopyrimidine ring at C5. The required 7-azaindole ring appropriately substituted is formed by a modified indole synthesis involving a nitrene insertion process (two steps). Formation of the annelated pyrimidine ring is achieved by two routes both involving a carbodiimide-mediated cyclization process, which allow incorporation of the amine functionality at C9 of the core tricyclic (six steps). Installation of the northeast 2-aminopyrimidine ring at C5 is performed using the Bredereck protocol (three steps). Ultimate, thermal decarboxylation with concomitant O-methyl deprotection and further N-benzyl deprotection by the action of triflic acid completed the synthesis of the target natural product variolin B.