trifluoroacetic acid in dichloromethane 0.333333 h; Ambient temperature;

1: 3-bromo-pyridine With lithium hexamethyldisilazane in tetrahydrofuran T=-15°C; Inert atmosphereReflux; 2: C19H17NO4S Diels-Alder reaction; Inert atmosphere; Further stages;

in 1,3,5-trimethyl-benzene 5 h; Heating;

1.1: conc. HCl; sodium nitrite / H2O / 0.5 h / 0 °C 1.2: 92 percent / potassium carbonate / H2O; acetonitrile / 0 - 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 2.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 2.3: 78 percent / Pd(PPh3)4 / tetrahydrofuran / Heating 3.1: 95 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 4.1: 63 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 1.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 1.3: 78 percent / Pd(PPh3)4 / tetrahydrofuran / Heating 2.1: 95 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 3.1: 63 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

sodium hydroxide; sodium tetrahydroborate in methanol; water 17 h; Heating; Yield given;

2: NaNO2/H+ 3: NaN3 4: Heating 5: 10 percent Pd-C / Heating View Scheme

1: NaNO2/H+ 2: NaN3 3: Heating 4: 10 percent Pd-C / Heating View Scheme

2: NaNO2/H+ 3: NaN3 4: Heating 5: 10 percent Pd-C / Heating View Scheme

in acetonitrile 36 h; Heating;