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6,7-Annulated-4-substituted indoles.
Reagents and conditions: (a) Br2, MeOH/CH2Cl2 (1:1), 95% or t-BuONO, CuBr2, 75%; (b) CH2=CHMgBr (3 equiv.) THF, −40 °C, 45% or NaH, MEI, THF, 0 °C, 88%; (c) n-BuLi (1.2 eqiv) PhMe, −78 °C to RT; (d) Et3N, CH2Cl2, RT, 94%; (e) R1B(OH)2 (1.5 equiv.) Cs2CO3 (2 equiv.), Pd2 (dba)3 (2mol%) S-Phos (8 mol %) 1 Butanol 150 °C, MW (14–70%); (f) NaOt-amylate (2 equiv.), Pd2(dba)3 (2 mol%) X-Phoa (8 mol%) DME, 150 °C, MW, 78%
