1: pyridine, 4-(dimethylamino)-pyridine / 17 h 2: 63 percent / BSA, TfOSiMe3 / 1,2-dichloro-ethane / 7 h / 70 °C 3: 96 percent / SOCl2 / dimethylformamide; CH2Cl2 / 5.5 h / 55 °C 4: 90 percent / tetrahydrofuran; methanol / 3 h / Ambient temperature 5: 78 percent / NaH / tetrahydrofuran / 9 h / 60 °C 6: 89 percent / NH3 / methanol / 6 h / 120 °C / 33752.7 Torr 7: 92 percent / H2, MgO / 5percent Pd/C / methanol / 65 h / 45 °C / 2250.2 Torr View Scheme

1: pyridine, 4-(dimethylamino)-pyridine / 17 h 2: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 3: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 4: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 5: 83 percent / NaH / tetrahydrofuran / 40 - 70 °C 6: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 7: 30percent NaOMe / methanol / Ambient temperature; pH 11 8: 94 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr View Scheme

1: pyridine, 4-(dimethylamino)-pyridine / 17 h 2: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 3: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 4: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 5: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 6: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 7: 30percent NaOMe / methanol / Ambient temperature; pH 11 8: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 9: pyridine / 5 h / Ambient temperature 10: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: pyridine / 1 h / -40 - 0 °C / Inert atmosphere 2: caesium carbonate / N,N-dimethyl-formamide / 5 h / 60 °C / Inert atmosphere 3: 10 Pd(OH)2 on carbon; hydrogen; triethylamine / methanol; ethyl acetate / 20 °C View Scheme