1: With potassium carbonate in ethanol; water; toluene T=20°C; 0.5 h; 2: With tetrakis(triphenylphosphine) palladium(0) in ethanol; water; toluene 10 h; Heating / reflux;

triethylamine in tetrahydrofuran; DMF (N,N-dimethyl-formamide) T=0 - 20°C; 16 h;

1: di-tert-butyl dicarbonate; 4-(N,N-dimethylamino)pyridine / 20 °C 2: H2; aq. HCl / Pd/C / methanol / 20 °C 3: 52 percent / K2CO3 / dimethylformamide / 70 - 80 °C 4: 60 percent / potassium tert-butoxide / toluene; 2-methyl-propan-2-ol / 90 °C 5: 14 percent / HCl / ethyl acetate / 12.5 h / 20 °C 6: SOCl2; DMF / tetrahydrofuran / 20 °C 7: Et3N / tetrahydrofuran; dimethylformamide / 20 °C 8: 50 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating View Scheme

1: H2; aq. HCl / Pd/C / methanol / 20 °C 2: 52 percent / K2CO3 / dimethylformamide / 70 - 80 °C 3: 60 percent / potassium tert-butoxide / toluene; 2-methyl-propan-2-ol / 90 °C 4: 14 percent / HCl / ethyl acetate / 12.5 h / 20 °C 5: SOCl2; DMF / tetrahydrofuran / 20 °C 6: Et3N / tetrahydrofuran; dimethylformamide / 20 °C 7: 50 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in ethanol; toluene Suzuki coupling; Heating;

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / Heating 1.2: tetrahydrofuran / 20 °C 2.1: aq. H2SO4 / tetrahydrofuran / 20 °C 3.1: 50 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating View Scheme

1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 2: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 2 h / 20 °C 2.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C View Scheme

1: sodium hydroxide / tetrahydrofuran; methanol; water / 1 h / Heating / reflux 2: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 3: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C View Scheme

1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C View Scheme