157396-16-2

Upstream product

• 157396-13-9 ethyl 4-(4-chlorophenylthio)-4-(1-phenylsulfonyl-1H-pyrrol-2-yl)butanoate 
• 157396-14-0 4-(4-chlorophenylthio)-4-(1-phenylsulfonyl-1H-pyrrol-2-yl)butanoyl chloride 
• 146564-01-4 ethyl 4-chloro-4-(4-chlorophenylthio)butanoate 
• 16851-82-4 N-phenylsulfonylpyrrole 
• 157396-11-7 7-(4-chlorophenylthio)-6,7-dihydro-1-(phenylsulfonyl)-1H-indol-4(5H)-one 

Downstream Products

• 95969-13-4 1-Benzenesulfonyl-4-hydroxy-1H-indole 

Relevant academic research and scientific papers

New, concise route to indoles bearing oxygen or sulfur substituent at the 4-position. Synthesis of (±)- and (S)-(-)-pindolol and (±)-chuangxinmycin

A new method for the synthesis of 4-alkoxy- and 4-[alkyl (or aryl)thio]indoles has been developed by using the indolone 3 as a common intermediate. The indolone 3 was prepared from N-(phenylsulfonyl)pyrrole (7) and the α-chlorosulfide 8 in four steps. Heating of a mixture of 3 and an appropriate alcohol in the presence of p-toluenesulfonic acid and cupric chloride afforded the 4-alkoxyindoles 11a-d. The method was applied to the synthesis of (±)-pindolol (19) and (S)-(-)-pindolol (20). Thiols also reacted with 3 in the presence of boron trifluoride to give 4-[aryl (or alkyl)thio]indoles 12, 21a, b, and 22a-d. The (indol-4-ylthio)acetate 22c was employed as a key intermediate for a concise total synthesis of (±)- chuangxinmycin (27).