sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride in ethanol; water; toluene T=120°C; 1 h; Inert atmosphereMicrowave irradiation;

sodium carbonate; PdCl2(PPh3)2 in ethanol; water; ethyl acetate; toluene

1.1: potassium acetate / chloroform / 0.17 h / 20 °C / Cooling with ice 1.2: 18 h / Reflux 2.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 40 h / 80 °C / Inert atmosphere 3.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane; 4-bromo-1H-indazole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate in dimethyl sulfoxide T=80°C; 40 h; Inert atmosphere; 2: 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]-pyrimidin-4-yl)morpholine With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate in ethanol; toluene T=130°C; Suzuki coupling; 1.5 h; Microwave irradiation;

1.1: trichlorophosphate / 10 h / Reflux 2.1: methanol / 1 h / 20 °C 3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 11 h / -78 - 20 °C 4.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 4.2: 12 h / 20 °C 5.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

1.1: 2 h / 190 °C 1.2: Heating 2.1: trichlorophosphate / 10 h / Reflux 3.1: methanol / 1 h / 20 °C 4.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 11 h / -78 - 20 °C 5.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 5.2: 12 h / 20 °C 6.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

1.1: methanol / 1 h / 20 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 11 h / -78 - 20 °C 3.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 3.2: 12 h / 20 °C 4.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 40 h / 80 °C / Inert atmosphere 2: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

1.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 11 h / -78 - 20 °C 2.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 2.2: 12 h / 20 °C 3.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme

1.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 1.2: 12 h / 20 °C 2.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme