Synthesis of 2,3-Diaryl-3H-pyrrolo[2,3-c]pyridin-3-ol Derivatives by the Reaction of Aryl(3-isocyanopyridin-4-yl)methanones with Aryl Grignard Reagents

✍ Scribed by Kazuhiro Kobayashi; Taketoshi Kozuki; Manami Konishi; Teruhiko Suzuki; Miyuki Tanmatsu; Hisatoshi Konishi

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 145 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201100079

✦ Synopsis

Abstract

The reaction of aryl(3‐isocyanopyridin‐4‐yl)methanones 1, easily prepared from commercially available pyridin‐3‐amine, with aryl Grignard reagents gave, after aqueous workup, 2,3‐diaryl‐3__H__‐pyrrolo[2,3‐c]pyridin‐3‐ols 2. These rather unstable alcohols were O‐acylated with Ac~2~O in pyridine in the presence of a catalytic amount of 4‐(dimethylamino)pyridine (DMAP) to afford the corresponding 2,3‐diaryl‐3__H__‐pyrrolo[2,3‐c]pyridin‐3‐yl acetates 3 in relatively good yields.