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The reaction of the bulky Eind-based dialumane, (Eind)HAl(<i>&#956;</i>-H)₂AlH(Eind) (<b>1</b>) (Eind = 1,1,3,3,5,5,7,7-octaethyl-<i>s</i>-hydrindacen-4-yl), with pyridines is described. When <b>1</b> was treated with pyridine (Py) in toluene, the Py adduct of aryldihydroalumane, Py&#8594;AlH₂(Eind) (<b>2</b>), was initially formed. Then, the hydroalumination of Py took place to yield the Py-bound aryl(1,4-dihydropyrid-1-yl)hydroalumane, Py&#8594;AlH(1,4-dihydropyrid-1-yl)(Eind) (<b>3</b>). A similar reaction with a stronger Lewis base, 4-pyrrolidinopyridine (PPy), produced the stable PPy adduct, PPy&#8594;AlH₂(Eind) (<b>4</b>). The resulting organoaluminum compounds have been fully characterized by NMR spectroscopy as well as X-ray crystallography. The reaction mechanism from <b>1</b> to <b>3</b> via <b>2</b> has been examined by deuterium labeling experiments using (Eind)DAl(<i>&#956;</i>-D)₂AlD(Eind) (<b>1-<i>d</i>₄</b>).