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Sunday 31 July 2016

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


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

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
Publication Date (Web): July 13, 2016
Copyright © 2016 American Chemical Society

Abstract

Abstract Image
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.

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