Utility of Japp-Klingemann reaction for the preparation of 5-carboxy-6-chloroindole via Fischer indole protocol

Yihui Chen; Masayuki Shibata; Manju Rajeswaran; Thamarapu Srikrishnan; Sundeep Dugar; Ravindra K. Pandey

doi:10.1016/j.tetlet.2007.01.148

Utility of Japp-Klingemann reaction for the preparation of 5-carboxy-6-chloroindole via Fischer indole protocol

Yihui Chen
, Masayuki Shibata
, Manju Rajeswaran
, Thamarapu Srikrishnan
, Sundeep Dugar
, Ravindra K. Pandey

Institute for Lasers Photonics and Biophotonics

Roswell Park Cancer Institute
Rutgers - The State University of New Jersey, New Brunswick
Eastman Kodak
Scios Pharmaceuticals

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

5-Carboxy-6-chloroindole, a precursor for p38 kinase inhibitor, was prepared from 4-amino-2-chloro-3-iodobenzoicacid by following the Japp-Klingemann synthetic approach. The structures of the key intermediates were also confirmed by X-ray analyses. Computational analysis was helpful in understanding the importance of the substituents at the cyclization step of the synthesis.

Original language	English
Pages (from-to)	2353-2356
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	13
DOIs	https://doi.org/10.1016/j.tetlet.2007.01.148
State	Published - Mar 26 2007

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title = "Utility of Japp-Klingemann reaction for the preparation of 5-carboxy-6-chloroindole via Fischer indole protocol",

abstract = "5-Carboxy-6-chloroindole, a precursor for p38 kinase inhibitor, was prepared from 4-amino-2-chloro-3-iodobenzoicacid by following the Japp-Klingemann synthetic approach. The structures of the key intermediates were also confirmed by X-ray analyses. Computational analysis was helpful in understanding the importance of the substituents at the cyclization step of the synthesis.",

author = "Yihui Chen and Masayuki Shibata and Manju Rajeswaran and Thamarapu Srikrishnan and Sundeep Dugar and Pandey, \{Ravindra K.\}",

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T1 - Utility of Japp-Klingemann reaction for the preparation of 5-carboxy-6-chloroindole via Fischer indole protocol

AU - Chen, Yihui

AU - Shibata, Masayuki

AU - Rajeswaran, Manju

AU - Srikrishnan, Thamarapu

AU - Dugar, Sundeep

AU - Pandey, Ravindra K.

PY - 2007/3/26

Y1 - 2007/3/26

N2 - 5-Carboxy-6-chloroindole, a precursor for p38 kinase inhibitor, was prepared from 4-amino-2-chloro-3-iodobenzoicacid by following the Japp-Klingemann synthetic approach. The structures of the key intermediates were also confirmed by X-ray analyses. Computational analysis was helpful in understanding the importance of the substituents at the cyclization step of the synthesis.

AB - 5-Carboxy-6-chloroindole, a precursor for p38 kinase inhibitor, was prepared from 4-amino-2-chloro-3-iodobenzoicacid by following the Japp-Klingemann synthetic approach. The structures of the key intermediates were also confirmed by X-ray analyses. Computational analysis was helpful in understanding the importance of the substituents at the cyclization step of the synthesis.

UR - https://www.scopus.com/pages/publications/33847420568

U2 - 10.1016/j.tetlet.2007.01.148

DO - 10.1016/j.tetlet.2007.01.148

M3 - Article

AN - SCOPUS:33847420568

SN - 0040-4039

VL - 48

SP - 2353

EP - 2356

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Utility of Japp-Klingemann reaction for the preparation of 5-carboxy-6-chloroindole via Fischer indole protocol

Abstract

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