TY - JOUR
T1 - Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles
AU - Parsons, Thomas
AU - Ghellamallah, C
AU - Male, Louise
AU - Spencer, Neil
AU - Grainger, Richard
PY - 2011/7/21
Y1 - 2011/7/21
N2 - Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester hydrolysis and decarboxylation. Application of these building blocks in syntheses of natural and non-natural 5,6-dibromoindole derivatives, including meridianin F and 5,6-dibromo- 2'-demethylaplysinopsin, is reported.
AB - Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester hydrolysis and decarboxylation. Application of these building blocks in syntheses of natural and non-natural 5,6-dibromoindole derivatives, including meridianin F and 5,6-dibromo- 2'-demethylaplysinopsin, is reported.
UR - https://publons.com/publon/32993812/
U2 - 10.1039/c1ob05522d
DO - 10.1039/c1ob05522d
M3 - Article
C2 - 21643565
VL - 9
SP - 5021
EP - 5023
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 14
ER -