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. Author manuscript; available in PMC: 2016 Jul 23.
Published in final edited form as: J Med Chem. 2015 Jul 9;58(14):5459–5475. doi: 10.1021/acs.jmedchem.5b00391

Scheme 3. a. Synthesis of 9.

Scheme 3

aReaction conditions: (a) Ac2O, pyridine, DMF, rt, 12 h, 79%; (b) POCl3, DMA, Et4NCl, reflux, 20 min, 86%; (c) CH2I2, I2, isoamylnitrite, 80 °C, 1 h, 95%; (d) NH3, MeOH, 70 °C, 24 h, 56%; (e) TBSCl, imidazole, DMAP, DMF, rt, 24 h, 97%; (f) Pd(OAc)2, CyJohnPhos, K3PO4, Ph(BOH)2, 100 °C, 12 h, 67%; (g) AcOH–THF–H2O (9:1:1), THF, 23 °C, 24 h, 70%; (h) DPPA, DBU, NaN3, 15-crown-5, 24 h, 85%; (i) Pd/C, MeOH, rt, 1 h; (j) NH2SO2NH2, dioxane, 90 °C, 3 h, 87% (2 steps); (k) 31, Cs2CO3, DMF, 0 °C to rt, 16 h; (l) 80% aq TFA, 0 °C, 3 h, 45% (2 steps from 41). Nonstandard abbreviations: CyJohnPhos = (2-biphenyl)dicyclohexylphosphine.