A novel one-step synthesis of 2-substituted 6-azaindoles from 3-amino-4-picoline and carboxylic esters

Jinhua J Song; Zhulin Tan; Fabrice Gallou; Jinghua Xu; Nathan K Yee; Chris H Senanayake

doi:10.1021/jo0506480

A novel one-step synthesis of 2-substituted 6-azaindoles from 3-amino-4-picoline and carboxylic esters

J Org Chem. 2005 Aug 5;70(16):6512-4. doi: 10.1021/jo0506480.

Authors

Jinhua J Song¹, Zhulin Tan, Fabrice Gallou, Jinghua Xu, Nathan K Yee, Chris H Senanayake

Affiliation

¹ Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. jsong@rdg.boehringer-ingelheim.com

PMID: 16050720
DOI: 10.1021/jo0506480

Abstract

Dilithiation of 3-amino-4-picoline (1) was achieved with sec-BuLi at room temperature. Condensation of the resulting dianion (2) with carboxylic esters afforded a wide range of 2-substituted 6-azaindoles in good yields.

MeSH terms

Aza Compounds / chemistry*
Carboxylic Acids / chemistry*
Chromatography, High Pressure Liquid
Esters / chemistry*
Indoles / chemistry*
Molecular Structure
Picolines / chemistry*

Substances

3-amino-4-picoline
6-azaindole
Aza Compounds
Carboxylic Acids
Esters
Indoles
Picolines