1: 93 percent / C5H5N 2: 88 percent / NH3 View Scheme

1: Et3N, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.75 h / Ambient temperature 2: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 3: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 4: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h View Scheme

1: Et3N, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.75 h / Ambient temperature 2: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 3: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 4: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h 5: 98 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C View Scheme

1: 93 percent / C5H5N 2: 88 percent / NH3 3: 73 percent / I2; Et3N / methanol View Scheme