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was ground together in a mortar and pestle at room
temperature a number times as indicated in Table 2.
In cases when the mixture stuck to the walls of the
mortar, it was taken off from the walls with a spatula
and grounding was done again. After completion of
the reaction, as indicated by TLC, the reaction mix-
ture was quenched with H2O (5 mL) and extracted
with EtOAc (2 × 10 mL). The combined organic layer
was separated and dried (Na2SO4), concentrated in
vacuo, and the product was purified by column chro-
matography on silica gel (EtOAc: n-hexane, 1:9) to
give pure bis(indolyl)methanes.
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Preparation of bis(indolyl)methanes through the
electrophilic substitution reactions of indoles with
aldehydes by using HTP and supported HTP as non-
toxic, inexpensive, and reusable catalyst was suc-
cessfully performed in high yields under solvent-
free conditions. This method is applicable to a wide
range of aldehydes, including aromatic, aliphatic,
α,β-unsaturated, and heterocyclic substrates. The
present procedure represents a clean, environment
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Heteroatom Chemistry DOI 10.1002/hc