lithium hydroxide hydrate; water in tetrahydrofuran T=20°C; 18 h; Inert atmosphere;

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 50 °C 2.1: 0.75 h / 0.28 - 32 °C / |Inert atmosphere 2.2: 3.33 h / 20 - 85 °C / |Inert atmosphere 2.3: 0.5 h / pH Ca.1 / |Inert atmosphere 3.1: hydrogen; 5 palladium on charcoal / isopropanol acetate; methanol / 2 h / 0 °C / 775.74 Torr 4.1: N-ethyl-N,N-diisopropylamine; benzenesulfonic Acid / acetonitrile / 20 - 50 °C / pH 8 - 9 4.2: 8 h / 20 °C 5.1: lithium hydroxide hydrate / tetrahydrofuran / 1 h / 0.14 - 40 °C 5.2: 20 °C / pH 1.9 View Scheme

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 50 °C 2.1: 0.75 h / 0.28 - 32 °C / |Inert atmosphere 2.2: 3.33 h / 20 - 85 °C / |Inert atmosphere 2.3: 0.5 h / pH Ca.1 / |Inert atmosphere 3.1: hydrogen; 5 palladium on charcoal / isopropanol acetate; methanol / 2 h / 0 °C / 775.74 Torr 4.1: N-ethyl-N,N-diisopropylamine; benzenesulfonic Acid / acetonitrile / 20 - 50 °C / pH 8 - 9 4.2: 8 h / 20 °C 5.1: lithium hydroxide hydrate / tetrahydrofuran / 1 h / 0.14 - 40 °C 5.2: 20 °C / pH 1.9 View Scheme

1.1: triethylamine / 2 h / 150 °C / Inert atmosphere 2.1: thionyl chloride / N,N-dimethyl-formamide / 1.5 h / 110 °C / Inert atmosphere 2.2: 4 h / 50 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 2 h / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine / ethanol / 1 h / Inert atmosphere; Reflux 6.1: Zhan 1b catalyst / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere 7.1: palladium 10 on activated carbon; hydrogen / 1,4-dioxane; methanol / 2 h 8.1: lithium hydroxide hydrate; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere View Scheme

1.1: thionyl chloride / N,N-dimethyl-formamide / 1.5 h / 110 °C / Inert atmosphere 1.2: 4 h / 50 °C / Inert atmosphere 2.1: hydrogenchloride / 1,4-dioxane / 2 h / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine / ethanol / 1 h / Inert atmosphere; Reflux 5.1: Zhan 1b catalyst / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere 6.1: palladium 10 on activated carbon; hydrogen / 1,4-dioxane; methanol / 2 h 7.1: lithium hydroxide hydrate; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere View Scheme

1.1: 1,1'-carbonyldiimidazole / 1 h / 20 - 25 °C 1.2: 2.5 h / 95 °C 2.1: 0.75 h / 0.28 - 32 °C / |Inert atmosphere 2.2: 3.33 h / 20 - 85 °C / |Inert atmosphere 2.3: 0.5 h / pH Ca.1 / |Inert atmosphere 3.1: hydrogen; 5 palladium on charcoal / isopropanol acetate; methanol / 2 h / 0 °C / 775.74 Torr 4.1: N-ethyl-N,N-diisopropylamine; benzenesulfonic Acid / acetonitrile / 20 - 50 °C / pH 8 - 9 4.2: 8 h / 20 °C 5.1: lithium hydroxide hydrate / tetrahydrofuran / 1 h / 0.14 - 40 °C 5.2: 20 °C / pH 1.9 View Scheme

1.1: 1,1'-carbonyldiimidazole / 1 h / 20 - 25 °C 1.2: 2.5 h / 95 °C 2.1: 0.75 h / 0.28 - 32 °C / |Inert atmosphere 2.2: 3.33 h / 20 - 85 °C / |Inert atmosphere 2.3: 0.5 h / pH Ca.1 / |Inert atmosphere 3.1: hydrogen; 5 palladium on charcoal / isopropanol acetate; methanol / 2 h / 0 °C / 775.74 Torr 4.1: N-ethyl-N,N-diisopropylamine; benzenesulfonic Acid / acetonitrile / 20 - 50 °C / pH 8 - 9 4.2: 8 h / 20 °C 5.1: lithium hydroxide hydrate / tetrahydrofuran / 1 h / 0.14 - 40 °C 5.2: 20 °C / pH 1.9 View Scheme

1.1: 0.75 h / 0.28 - 32 °C / |Inert atmosphere 1.2: 3.33 h / 20 - 85 °C / |Inert atmosphere 1.3: 0.5 h / pH Ca.1 / |Inert atmosphere 2.1: hydrogen; 5 palladium on charcoal / isopropanol acetate; methanol / 2 h / 0 °C / 775.74 Torr 3.1: N-ethyl-N,N-diisopropylamine; benzenesulfonic Acid / acetonitrile / 20 - 50 °C / pH 8 - 9 3.2: 8 h / 20 °C 4.1: lithium hydroxide hydrate / tetrahydrofuran / 1 h / 0.14 - 40 °C 4.2: 20 °C / pH 1.9 View Scheme

1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine / ethanol / 1 h / Inert atmosphere; Reflux 3: Zhan 1b catalyst / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / 1,4-dioxane; methanol / 2 h 5: lithium hydroxide hydrate; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere View Scheme

1: sodium hydrogencarbonate / dichloromethane; water / 2 h / Inert atmosphere; Cooling with ice 2: 4-(N,N-dimethlyamino)pyridine / toluene / 6 h / Inert atmosphere; Reflux 3: lithium hydroxide hydrate; water / methanol / 4 h / 60 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine / ethanol / 1 h / Inert atmosphere; Reflux 6: Zhan 1b catalyst / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere 7: palladium 10 on activated carbon; hydrogen / 1,4-dioxane; methanol / 2 h 8: lithium hydroxide hydrate; water / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere View Scheme