sodium hydride in tetrahydrofuran 4 h; Heating;

1: 4-fluoro-benzoic acid With 1,1'-carbonyldiimidazole in tetrahydrofuran T=20°C; 10 h; 2: magnesium salt of monomethyl malonic acid in tetrahydrofuran T=20°C; 18 h; Further stages.;

palladium(II) 2,4-pentanedionate; tributyl-amine; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene T=90°C; P=7500.75 Torr; 15 h; Inert atmosphereAutoclaveSchlenk technique;

ammonium acetate in methanol T=20°C; 60 h;

hydrogenchloride in methanol T=0 - 20°C; Pechmann condensation; 15 h;

bromine in dichloromethane T=0°C; 1 h;

sodium hydrogencarbonate; ammonium chloride in ethanol 4 h; Reflux;

hydrazine in ethanol; water T=20 - 80°C; 1 h;

1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere 2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere 3.1: nitric acid / chloroform / 1 h / -15 - 0 °C 4.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 21 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 6.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 7.2: 18 h / 21 °C View Scheme

1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere 2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere 3.1: nitric acid / chloroform / 1 h / -15 - 0 °C 4.1: boron trichloride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere 4.2: Cooling with ice 5.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.83 h / 0 °C / Inert atmosphere 6.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 18 h / 100 °C / Inert atmosphere 7.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethyl acetate; water / 16 h / 21 °C 8.1: triethylamine / dichloromethane / 2 h / 0 °C / Cooling with ice 9.1: potassium hydroxide; water / ethanol / 1 h / Reflux View Scheme