benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine in dichloromethane T=0 - 20°C;

PyAOP in dichloromethane T=0 - 20°C; 3.75 h;

1.1: Mg; I2 / tetrahydrofuran / Heating 1.2: 60 percent / tetrahydrofuran / -40 - 0 °C 2.1: Et3SiH; TFA / 0 - 20 °C 3.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 4.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 5.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 5.2: 61 percent / tetrahydrofuran / -70 - -50 °C 6.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C 7.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme

1.1: 79 percent / Pd(OAc)2; PPh3; aq. Na2CO3 / acetone / 18 h / Heating 2.1: Mg; I2 / tetrahydrofuran / Heating 2.2: 60 percent / tetrahydrofuran / -40 - 0 °C 3.1: Et3SiH; TFA / 0 - 20 °C 4.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 5.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 6.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 6.2: 61 percent / tetrahydrofuran / -70 - -50 °C 7.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C 8.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme

1: 81 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; N-methylmorpholine; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 2 - 20 °C 2: 97 percent / HCl(gas) / CH2Cl2; dioxane / 4 - 20 °C 3: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme

1: 81 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; N-methylmorpholine; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 2 - 20 °C 2: 97 percent / HCl(gas) / CH2Cl2; dioxane / 4 - 20 °C 3: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme

1: 97 percent / HCl(gas) / CH2Cl2; dioxane / 4 - 20 °C 2: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme

1: sodium carbonate / palladium diacetate; triphenylphosphine / water; acetone / 18 h / Heating / reflux 2: n-ethyl morpholine / acetonitrile / 16.5 h / Heating / reflux 3: hydrogen / palladium 10 on activated carbon / ethanol; water / 6 h / 20 °C / 2250.23 Torr 4: PyAOP / dichloromethane / 3.75 h / 0 - 20 °C View Scheme

1.1: Mg; I2 / tetrahydrofuran / Heating 1.2: 60 percent / tetrahydrofuran / -40 - 0 °C 2.1: Et3SiH; TFA / 0 - 20 °C 3.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 4.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 5.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 5.2: 61 percent / tetrahydrofuran / -70 - -50 °C 6.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C 7.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme

1.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 2.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 3.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 3.2: 61 percent / tetrahydrofuran / -70 - -50 °C 4.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C 5.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme