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. Author manuscript; available in PMC: 2020 Jul 24.
Published in final edited form as: J Med Chem. 2019 May 24;62(11):5330–5357. doi: 10.1021/acs.jmedchem.8b01709

Scheme 1. Synthesis of Benzaldehyde Intermediates 2–8a.

Scheme 1.

aReagents and conditions: (a) bromobenzene for 2 and 2-chlorothiazole for 3, Pd(PPh3)4, K2CO3, H2O, THF, 80°C, 12 h; (b) NaN3, Et3N, DMF, 180°C, overnight for 4; (c) NaN3, Et2NH.HCl, toluene, reflux, 24 h for 5 and 6; (d) 4, CH3I, K2CO3, DMF, rt, 4 h; (e) pyrimidin-2-yl-piperazine, K2CO3, DMF, 130°C, 24 h.