[Intramolecular alkylaton of aromatic compounds. 34. Synthesis  of pyridinylmethylindolines as potential precursors of  ergolines]  .
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.
Reimann
E
E
Department für Pharmazie, Zentrum für Pharmaforschung der Ludwig-Maximilians-Universität München, Germany. ebrei@cup.uni-muenchen.de
Erdle
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W
D004873:Ergolines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D004873:Ergolines; D007202:Indicators and Reagents; D007211:Indoles; D011725:Pyridines