Scheme 1.
Reagents and conditions: (a) tert-butylnitrite, CuBr2, CH3CN, 90 °C, 24 h; (b) (1) CsF, DMSO, N2, 170 °C, 5 h; (2) (CH3)2NH (ac) 40%, K2CO3, 70 °C, 17 h; (c) (1) NaBH4, 2-propanol, reflux, 12 h; (2) HCl (ac) 37%; (d) CuCN, DMF, N2, reflux 12 h; (e) CH3(CH2)6CH2MgBr, CuBr (cat.), THF, N2, room temperature, 1 h.
