74459-27-1Relevant academic research and scientific papers
Selective lithiation of 2,3-dibromo-1-methylindole. A synthesis of 2,3-disubstituted indoles
Liu, Yanbing,Gribble, Gordon W
, p. 7135 - 7137 (2007/10/03)
Indole (1) can be converted to 2,3-dibromo-1-methylindole (3) in two operations (92% yield). Treatment of 3 with tert-butyllithium effects clean monolithiation to 3-bromo-2-lithio-1-methylindole (4), which can be trapped with various electrophiles to afford the 3-bromo-2-substituted indoles (5-8) in 85-99% yield. A second bromine-lithium exchange reaction and quenching with electrophiles yields the 2,3-disubstituted indoles (9-10) in 88-95% yield.
