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. Author manuscript; available in PMC: 2015 Mar 3.
Published in final edited form as: Chembiochem. 2014 Jan 23;15(4):595–611. doi: 10.1002/cbic.201300723

Scheme 4.

Scheme 4

Convergent synthesis of constrained indazole-based 4EGI-1 mimetic via N-arylation of 1H-indazole-3-carboxylic acid by 2-halo-4-phenylthiazole. Reagents and conditions: i) KSCN (2 eq), acetonitrile, reflux, overnight; ii) HCl(g) or HBr (g), dry ether, 0 °C to rt, overnight; iii) HNO3/H2SO4 (conc.); iv) 1H-indazole-3-carboxylic acid or 5-nitro-1H-indazole-3-carboxylic acid, NaOH (2.2 eq) in DMSO, N2.