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. 2013 Oct 28;56(22):9310–9327. doi: 10.1021/jm401399c

Scheme 7. Synthesis of RB- 054 from 4-Iodoaniline.

Scheme 7

Reagents and conditions: (a) 1-octyne, Pd(PPh3)4, CuI, Et3N, 60 °C, 12 h; (b) (i) 10% aq HCl, NaNO2; (ii) NaN3; (c) 3-ethynylpyridine, sodium ascorbate, CuSO4, t-BuOH/H2O (1:1); (d) Pd/C, H2, EtOAc, rt, 2 days.