53904-14-6

Basic information

• Product Name: pyrrolo[3,2,1-de]phenanthridin-7-one
• Synonyms: pyrrolo[3,2,1-de]phenanthridin-7-one
• CAS NO: 53904-14-6
• Molecular Weight: 219.243
• Mol File: 53904-14-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: pyrrolo[3,2,1-de]phenanthridin-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: pyrrolo[3,2,1-de]phenanthridin-7-one(53904-14-6)
• EPA Substance Registry System: pyrrolo[3,2,1-de]phenanthridin-7-one(53904-14-6)

Safety Data

• Hazardous Substances Data: 53904-14-6(Hazardous Substances Data)

Upstream product

• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 548775-84-4 7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trimethylsilanyl-indole-1-carboxylic acid diethylamide 

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.