1: N,N-dimethylpyridin-4-amine / pyridine 2: aq. NaOH / dioxane 3: 98 percent / K2CO3 / acetone 4: aq. NaOH / dioxane View Scheme

1.1: Pd2(dba)3*CHCl3; (1R,2R)-bis[2-(di-Ph-phosphinyl)-benzamino]-1,2-di-Ph-ethane / CH2Cl2 / 4 h / 20 °C 2.1: PdCl2(CH3CN)2; 1,2,2,6,6-pentamethylpiperidine; formic acid / dimethylformamide / 6 h / 50 °C 3.1: 96 percent / TEA / CH2Cl2 4.1: 92 percent / NBS / tetrahydrofuran / 20 °C 5.1: DIBAL-H / CH2Cl2 / -78 °C 6.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C 6.2: 368 mg / tetrahydrofuran / 20 °C 7.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C 8.1: 910 mg / imidazole / CH2Cl2 / 2 h / Heating 9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 9.2: tetrahydrofuran; hexane / 1 h / -78 °C 10.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h 11.1: toluene / 3.5 h / 110 °C 11.2: 64 percent / air / toluene / 2 h / 20 °C 12.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C View Scheme

1.1: 89 percent / K2CO3; 18-crown-6 / acetone / 15 h / Heating 2.1: Mg / diethyl ether / 1 h / Heating 2.2: 44 percent / [Ni(dppe)Cl2] / diethyl ether / 5 h / Heating 3.1: 80 percent / H2 / Pd/C / methanol / 20 °C View Scheme