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. 2024 Mar 18;67(6):4707–4725. doi: 10.1021/acs.jmedchem.3c02308

Scheme 4. Synthesis of Compounds M4K2308 (32) and M4K2281 (33).

Scheme 4

Reagents and conditions: (a) Pd(dppf)Cl2, K2CO3, 1,4-dioxane/H2O, 100 °C, 16 h, 35%; (b) LiHDMS, THF, 0 °C to rt, 1 h, 96%; (c) HCl, rt, 1 h, 85%; (d) NaBH4, THF/MeOH, 0 °C, 2 h, 77%; (e) BBr3, DCM, −78 °C to rt, 24 h, 62%; (f) triphenylphosphine, diisopropyl azodicarboxylate, THF, 0 °C to rt, 1.5 h, 68%; (g) Pd(dppf)Cl2, K2CO3, 1,4-dioxane/H2O, 100 °C, 2 h, 73%; (h) RuPhos Pd G3, NaOtBu, 1,4-dioxane, 100 °C, 16 h; (i) TFA, DCM, rt, 1 h, 29% over two steps; (j) RuPhos Pd G3, NaOtBu, 1,4-dioxane, 100 °C, 16 h, 49%.