Intramolecular alkylaton of aromatic compounds. 34. Synthesis of pyridinylmethylindolines as potential precursors of ergolines) .

摘要

The carbinoles 3 prepared from the N-protected indolaldehydes 2 and bromomethoxypyridine 1 can smoothly be hydrogenolized to the lutidinylindoles 4 which in turn give the corresponding indolines 5 by NaCNBH3-reduction. Treatment of 3a by acid the trihetarylmethane 9 and 5-methoxypyridine-2-carboxaldehyde 10 are generated. The acetylpyridine 7 is found as a by-product of 3c. As by-product of the reduction the borane adduct 8 is detected.