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. 2014 Sep 25;57(20):8378–8397. doi: 10.1021/jm500827t

Scheme 1. Synthesis of S-Substituted N-(4-Fluoro-phenyl)-6-mercapto-nicotinamides 9–45, 47–48, 52, and 55.

Scheme 1

Conditions: (i) 4-fluoroaniline, EEDQ, DMF, rt; (ii) method A: Br-CH2–R, solid-phase base (N-methylmorpholino-substituted resin), DMF, 60 °C; method B: Br-CH2–R or Cl-CH2–R, DMF, base (TEA, DIPEA, or), rt; method C: Br-CH2–R, EtOH, 1 N NaOH, reflux.