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. 2014 Jul 17;58(1):183–196. doi: 10.1021/jm500480k

Scheme 2. Synthesis of (E)-N-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(2-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)vinyl)-4-methylbenzamide 2.

Scheme 2

Reagents and conditions: (a) 29, HATU, DMAP, DIEA, CH2Cl2; (b) NaOMe, MeOH, 60 °C; (c) MePPh3I, n-BuLi, THF, −78 °C to rt; (d) (i) TFA, DCM, (ii) LiOH, H2O/THF; (e) Boc2O, DMAP, CH2Cl2; (f) 32, Pd2(dba)3, P(t-Bu)3, DIEA, 80 °C; (g) TFA/CH2Cl2, 0 °C.