2-Chloro-5-(4-(methylsulfonyl)phenyl)pyrazine

1H NMR (DMSO-d6, 400 MHz) δ 9.24 (d, J = 1.5 Hz, 1H), 8.93 (d, J = 1.2 Hz, 1H), 8.38 (d, J = 8.5 Hz, 2H), 8.09 (d, J = 8.5 Hz, 2H), 3.29 (s, 3H).
13C NMR (100.6 MHz, DMSO-d6) 149.0, 148.5, 144.6, 142.7, 142.4, 139.8, 128.2, 128.1, 43.9.
HRMS calcd for C11H10ClN2O2S (M + H)+ 269.0146, found, 269.0143.

Paper

Development of Large-Scale Routes to Potent GPR119 Receptor Agonists

Richard T. Matsuoka*†, Eric E. Boros#, Andrew D. Brown†, Kae M. Bullock†, Will L. Canoy‡, Andrew J. Carpenter#, Jeremy D. Cobb†,Shannon E. Condon†, Nicole M. Deschamps†, Vassil I. Elitzin†, Greg Erickson†,Jing M. Fang#, David H. Igo§, Biren K. Joshi‡, Istvan W. Kaldor#, Mark B. Mitchell†, Gregory E. Peckham#, Daniel W. Reynolds‡, Matthew C. Salmon†, Matthew J. Sharp†, Elie A. Tabet#, Jennifer F. Toczko†, Lianming Michael Wu‡, and Xiao-ming M. Zhou†

†API Chemistry Department, ‡Analytical Science & Development Department, #Medicinal Chemistry Department, and§Particle Sciences and Engineering Department, GlaxoSmithKline, 709 Swedeland Road, King of Prussia, Pennsylvania 19406, United States

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.6b00157, http://pubs.acs.org/doi/abs/10.1021/acs.oprd.6b00157

Publication Date (Web): July 13, 2016

*E-mail: richard.t.matsuoka@gsk.com.

Abstract

Practical and scalable syntheses were developed that were used to prepare multikilogram batches of GSK1292263A (1) and GSK2041706A (15), two potent G protein-coupled receptor 119 (GPR119) agonists. Both syntheses employed relatively cheap and readily available starting materials, and both took advantage of an SNAr synthetic strategy.

Supporting Info

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KHAJURAHO, MADHYA PRADESH, INDIA

Khajuraho Group of Monuments

The Khajuraho Group of Monuments is a group of Hindu and Jain temples in Madhya Pradesh, India, about 175 kilometres southeast of Jhansi. They are one of the UNESCO World Heritage Sites in India.Wikipedia