A concise and regioselective synthesis of 6-bromo-5-methoxy-1H-indole-3-carboxylic acid and its derivatives: Strategic development toward core moiety of Herdmanine D

doi:10.1080/00397911.2020.1718162

Paper

A concise and regioselective synthesis of 6-bromo-5-methoxy-1H-indole-3-carboxylic acid and its derivatives: Strategic development toward core moiety of Herdmanine D

Published Feb 3, 2020 · Pankaj Sharma, Nutan Sharma, Gunjan Kashyap

Synthetic Communications

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Abstract

Abstract A concise, regioselective and highly efficient strategy for the construction of 6-bromo-5-methoxy-1H-indole-3-carboxylic acid has been developed through trifluoroacetylated indole driven hydrolysis. The developed protocol has the advantage of selectively directing bromine substituent on one position. The formation of this regioselective product was confirmed by 1HNMR data. The attractive feature of this new strategy is that the 6-bromo-5-methoxy-1H-indole-3-carboxylic acid is an important scaffold of anti-inflammatory naturally occurring compound Herdmanine D. Furthermore, bromo indoles bearing carboxylic acid group were further functionalized in amide derivatives by using various aromatic/aliphatic amines through ultrasonic irradiation. Graphical Abstract

Study Snapshot

This study developed a regioselective strategy for the construction of 6-bromo-5-methoxy-1H-indole-3-carboxylic acid, which is an important scaffold for the anti-inflammatory compound Herdmanine D, using trifluoroacetylated ind

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

A concise and regioselective synthesis of 6-bromo-5-methoxy-1H-indole-3-carboxylic acid and its derivatives: Strategic development toward core moiety of Herdmanine D

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