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. 2018 Apr 13;9(7):667–672. doi: 10.1021/acsmedchemlett.8b00134

Scheme 1. General Synthetic Route to Benzo[b]thiophene Compounds.

Scheme 1

Reagents and conditions: (a) DMF, SOCl2, 80 °C, 4 h, then NH3, H2O, THF, 0 to 25 °C, 16 h; (b) TFAA, pyridine, ClCH2CH2Cl, 25 °C, 1.5 h; (c) NH2OH, H2O, EtOH, 90 °C, 48 h; (d) ROCl, pyridine, 0 to 120 °C, 16 h; (e) BBr3, CH2Cl2, −78 to 25 °C, 16 h; (f) 11, neat, 150 °C, 60 h; (g) DMF, SOCl2, 45 to 75 °C, 72 h, then CH3NH2, H2O, THF, 0 to 25 °C, 4 h.