1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 4.1: N,N-dimethyl-formamide / 95 - 100 °C 4.2: 0 - 5 °C / pH 8 - 9 View Scheme

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 View Scheme

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 4.1: N,N-dimethyl-formamide / 95 - 100 °C 4.2: 0 - 5 °C / pH 8 - 9 5.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 6.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C 7.1: hydrogen; methanesulfonic acid / 5 palladium on charcoal / acetone / 20 °C / 2585.81 Torr 7.2: 0.5 h / 25 - 30 °C View Scheme

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 4.1: N,N-dimethyl-formamide / 95 - 100 °C 4.2: 0 - 5 °C / pH 8 - 9 5.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 6.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C 7.1: hydrogen; methanesulfonic acid / 5 palladium on charcoal / acetone / 20 °C / 2585.81 Torr 7.2: 0.5 h / 25 - 30 °C 8.1: hydrogen bromide / dichloromethane; water; ethylene glycol / 0.5 h / 5 - 10 °C / Inert atmosphere View Scheme

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 4.1: N,N-dimethyl-formamide / 95 - 100 °C 4.2: 0 - 5 °C / pH 8 - 9 5.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 6.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme