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. 2018 Sep 14;9(10):1013–1018. doi: 10.1021/acsmedchemlett.8b00283

Scheme 3. Synthesis of 4-Chloroindazole Inhibitor 18.

Scheme 3

Reagents and conditions: (a) tetramethylethylenediamine (TMEDA), n-BuLi, THF, −75 °C, 2 h; (b) Me3SiCl, THF, −75 °C, overnight; (c) AlCl3, CH2Cl2, 0 °C; (d) 4-chlorobutanoyl chloride, −80 to −10 °C, 4 h; (e) NaN3, DMF, 50 °C, 16 h; (f) hydrazine monohydrate, dimethoxyethane (DME), reflux, 17 h; (g) NaH, DMF, 0 °C, 30 min to 1 h; (h) cyclopentylmethyl bromide, DMF, 0 °C to rt, 1 to 2 h; (i) SnCl2, CH3OH, 2.5 h; (j) ethyl-2-chloroacetamidate·HCl, Et3N, CH3OH, rt, 1 to 2 h.