triethylamine in tetrahydrofuran T=25°C; 2 h;

1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 2: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 3: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 4: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 5: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 6: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 7: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C View Scheme

1: 42 percent 2: SOCl2 / dimethylformamide / 2 h / Heating 3: Et3N / CHCl3 / 1 h / Ambient temperature View Scheme

1: 67 percent / potassium carbonate / acetone / 6 h / Heating 2: 77 percent / H2 / Pd/C / atmospheric pressure 3: 2,2-diphenyl-1-picrylhydrazyl / tetradeuteriomethanol; acetone-d6 / 0.17 h View Scheme

1: 100 percent / K2CO3 / acetone / 17 h / 20 °C 2: 61 percent / POCl3 / 16 h / 70 °C View Scheme

potassium carbonate in acetone T=20°C; Methylation; 17 h;

potassium carbonate in acetone 6 h; Heating;

1: 1.) NaH / 1.) DMF, 0 degC, 2.) r.t., 30min 2: H2 / 10percent Pd/C / ethyl acetate / 15 h / Ambient temperature View Scheme

1: 67 percent / potassium carbonate / acetone / 6 h / Heating 2: 77 percent / H2 / Pd/C / atmospheric pressure View Scheme