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. 2015 Feb 5;58(5):2489–2512. doi: 10.1021/jm501997q

Scheme 7. Synthesis of 2-Hydroxypropyl-5-methoxyindole-pyridinylpropenone 2q.

Scheme 7

Reagents and conditions: (a) MnO2, EtOAc, reflux; (b) Ph3PCHCO2C2H5, THF, rt; (c) 1. LiAlH4, THF, 0 °C to rt; 2. H2, Pd/C, EtOAc/MeOH; (d) 30, acetic anhydride, TEA, CH3CN, rt; (e) 1. POCl3, DMF; 2. 1 N NaOH; (f) 4-acetylpyridine, piperidine, MeOH, reflux.