1: H2SO4; HNO2 2: zinc-powder; aq.-ethanolic acetic acid View Scheme

C27H36Cl2N2Zn; phenyl silane in tetrahydrofuran T=100°C; 20 h;

hydrogenchloride; sodium nitrite T=0 - 5°C;

pyridine in dichloromethane T=-30 - 20°C; Inert atmosphere;

pyridine; xylene

pyridine in diethyl ether 1.) -78 deg C, 1 min, 2.) RT;

1: 70 percent / pyridine / diethyl ether / 1.) -78 deg C, 1 min, 2.) RT 2: 71 percent / HCl gas / CHCl3 / 192 h / Ambient temperature View Scheme

1: 26 g / pyridine / CH2Cl2 / 1 h / 0 °C 2: 26.8 g / NBS, AIBN / CCl4 / 3 h / Heating 3: 34 g / toluene / 36 h / Heating 4: 1) t-BuOK / 1) THF, 0 deg C, 30 min, 2) THF, 0 deg C, 4 h 5: H2, NaHCO3 / 10percent Pd/C / methanol / 760 Torr 6: 14.2 g / KOH / ethanol / Heating 7: 83 percent Turnov. / pyridine / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) r.t., 3 h 8: DOWEX-50X8-400R, MeOH / 20 h / 50 °C 9: Et3N / CH2Cl2 / 1 h / 0 °C 10: 10.6 g / LiI / dimethylformamide / 3.5 h / 90 °C 11: 72 percent Turnov. / AgNO2 / diethyl ether / 1.) 0 deg C, 1 d, 2.) r.t., 12 d, in darkness View Scheme

1.1: 98 percent / K2CO3 / acetonitrile / 4 h / Heating 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 25 percent / B(OCH3)3 / tetrahydrofuran / -78 - 20 °C View Scheme

(i) CH2Cl2, (ii) /BRN= 507502/; Multistep reaction;