Scheme 4.
Reagents and conditions: a) CuI, K3PO4, N-(2-cyanophenyl)picolinamide, 21, DMSO, 18%; b) Cu(OAc)2, TMEDA, 14, DMSO, 87%; c) 10% Pd/C, H2, MeOH/THF (1:1), 85%; d) K2CO3, 49, DMF, 84%; e) TMSCl, NaI, MeCN, 45%.
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