1-(2-Methoxy-4-nitrophenyl)-4-(p-tolyl)-1H-1,2,3-triazole

1-(2-Methoxy-4-nitrophenyl)-4-(p-tolyl)-1H-1,2,3-triazole (3a), (Table 2, entry 1):
Using method A described above with 2-methoxy-4-nitroaniline
(1a). After purification by flash column
chromatography (25% AcOEt/hexanes, Rf = 0.45), 359 mg
of 3a (79%) were obtained as a yellow solid. Mp > 190 °C;

1H-NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 8.16 (d, J = 8.8
Hz, 1H), 8.05 (d, J = 8.8 Hz, 1H), 7.97 (s, 1H), 7.79 (d, J = 7.8 Hz, 2H), 7.26 (d, J =
7.8 Hz, 2H), 4.08 (s, 3H) 2.41 (s, 3H) ppm;

13C{1H} NMR (100 MHz, CDCl3) δ 150.6,
148.1, 148.0, 138.6, 131.1, 129.7, 127.3, 125.9, 125.1, 121.1, 116.8, 108.0, 57.0,
21.4 ppm; HRMS (EI) calcd. for C16H13NO3 310.1066 [M+]; found 310.1060.

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.6b00292

Handling Hazards Using Continuous Flow Chemistry: Synthesis of N1-Aryl-[1,2,3]-triazoles from Anilines via Telescoped Three-Step Diazotization, Azidodediazotization, and [3 + 2] Dipolar Cycloaddition Processes

Matthieu Teci†, Michael Tilley†, Michael A. McGuire*‡, and Michael G. Organ*†§

† Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J1P3, Canada

‡ GlaxoSmithKline Pharmaceuticals Inc., 709 Swedeland Road, P.O. Box 1539, UMW 2810, King of Prussia, Pennsylvania 19406, United States

§ Centre for Catalysis Research and Innovation (CCRI) and Department of Chemistry, University of Ottawa, Ottawa, Ontario K1N6N5, Canada

Org. Process Res. Dev., Article ASAP

http://pubs.acs.org/doi/suppl/10.1021/acs.oprd.6b00292

Michael G. Organ Professor of Chemistry, York University, Toronto, Canada

Webpage: http://www.yorku.ca/organ/ Education: B. Sc. (Honours) in Biology (1986) from the University of Guelph; M. Sc. in Botany (1988) from the University of Guelph; Ph.D. in Chemistry (1992) from the University of Guelph. Professional Career: 1992-1994 NSERC Post-Doctoral Fellow with Barry Trost at Stanford University; 1994-1997 Faculty member at IUPUI in Indianapolis; 1997-present Faculty member at York University in Toronto. Awards and Honours: Author Profile in Angewandte Chemie, November 2013; Appointed to the Editorial Board of Chemistry, A European Journal, November 2013; NSERC Accelerator Award, April 2013; Agilent Labs Fellow, October 2011; Japan Society for the Promotion of Science (JSPS) Fellow, May 2010; Naeja Pharmaceuticals Lecturer, University of Alberta, March 2008; Merck-Frosst Canadian Academic Development Program Fellow, December 2007; International Xerox Foundation Fellow, July 2007; E.T.S. Walton Visitor Award (Ireland), May 2002; 1999 Premier's Research Excellence Award. Research Interests: Synthetic efficiency, catalysis, flow chemistry, sustainable manufacturing.

Department of Chemistry, York University

4700 Keele Street, Toronto, Ontario, Canada M3J 1P3

Phone: 416-736-5313. Facsimile: 416-736-5936. E-mail: organ@yorku.ca

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