88720-89-2

Basic information

• Product Name: 7H-Pyrrolo[3,2,1-de]phenanthridin-7-one,9,- 10-dimethoxy-
• CAS NO: 88720-89-2
• Molecular Weight: 279.295
• Mol File: 88720-89-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 7H-Pyrrolo[3,2,1-de]phenanthridin-7-one,9,- 10-dimethoxy- (CAS DataBase Reference)
• NIST Chemistry Reference: 7H-Pyrrolo[3,2,1-de]phenanthridin-7-one,9,- 10-dimethoxy- (88720-89-2)
• EPA Substance Registry System: 7H-Pyrrolo[3,2,1-de]phenanthridin-7-one,9,- 10-dimethoxy- (88720-89-2)

Safety Data

• Hazardous Substances Data: 88720-89-2(Hazardous Substances Data)

Upstream product

• 105875-33-0 2-bromo-N,N-diethyl-4,5-dimethoxy-benzamide 
• 548775-84-4 7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trimethylsilanyl-indole-1-carboxylic acid diethylamide 
• 194231-75-9 (7-Bromo-indol-1-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 179536-94-8 (E)-3-(8,9-Dimethoxy-6-oxo-6H-phenanthridin-5-yloxy)-acrylic acid methyl ester 

Downstream Products

• 80787-57-1 pratorinine 

Relevant articles and documents

Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids

(Matrix presented) Although the indole N-phosphinoyl derivative 4 undergoes n-BuLi deprotonation/electrophile quench to afford C-7-substituted products, its deprotection requires harsh conditions. On the other hand, the N-amide 12, upon sequential or one-pot C-2 metalation, silylation, C-7 metalation, and electrophile treatment, furnishes indoles 7 in good overall yields. In combination with the Suzuki-Miyaura protocol, C-7 aryl (heteroaryl)-substituted indoles 14 and 16 are obtained, including hippadine and pratosine, members of the pyrrolophenanthridone alkaloid family.

A synthesis of the amaryllidaceae alkaloid pratosine

A synthesis of pratosine by thermolysis of the Michael adduct obtained from 5-hydroxy-8,9-dimethoxy-6(5H)-phenanthridone and methyl propiolate is described.