pyridine hydrochloride T=160°C; 6 h;

1: 95 percent / Pd(CF3COO)2, P(C6H5)3, i-Pr2NH, CF3COOAg / tetrahydrofuran / 90 °C 2: 77 percent / Zn, conc. aq. HCl, N-methylpyrrolidinone 3: 92 percent / H2SO4 4: 99 percent / Ag2O 5: 44 percent / (Me3Sn)2, (Ph3P)4Pd / 168 h / 100 °C 6: 77 percent / Py*HCl / 6 h / 160 °C View Scheme

1: 94 percent / NBS 3: H2O2 4: 95 percent / Pd(CF3COO)2, P(C6H5)3, i-Pr2NH, CF3COOAg / tetrahydrofuran / 90 °C 5: 77 percent / Zn, conc. aq. HCl, N-methylpyrrolidinone 6: 92 percent / H2SO4 7: 99 percent / Ag2O 8: 44 percent / (Me3Sn)2, (Ph3P)4Pd / 168 h / 100 °C 9: 77 percent / Py*HCl / 6 h / 160 °C View Scheme

2: H2O2 3: 95 percent / Pd(CF3COO)2, P(C6H5)3, i-Pr2NH, CF3COOAg / tetrahydrofuran / 90 °C 4: 77 percent / Zn, conc. aq. HCl, N-methylpyrrolidinone 5: 92 percent / H2SO4 6: 99 percent / Ag2O 7: 44 percent / (Me3Sn)2, (Ph3P)4Pd / 168 h / 100 °C 8: 77 percent / Py*HCl / 6 h / 160 °C View Scheme

1.1: 54 percent / DMAP; pyridine / CH2Cl2 / 12 h / 20 °C 2.1: 93 percent / NBS; AIBN / CCl4 / 3 h / Heating 3.1: NaH / tetrahydrofuran / 0.5 h / 20 °C 3.2: 87 percent / tetrabutylammonium iodide / tetrahydrofuran / 5 h / 20 °C 4.1: 89 percent / NaOH / ethanol / 12 h 5.1: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h 6.1: 82 percent / PdCl2(dppf) / dioxane / 3 h / 90 °C 7.1: 95 percent / HCl / tetrahydrofuran / 3 h / Heating 8.1: 100 percent / K2CO3 / propan-2-ol; CH2Cl2 / 5 h / 45 °C 9.1: 87 percent / AlCl3; NaCl / 0.08 h / 150 °C 10.1: 69 percent View Scheme

1.1: 93 percent / NBS; AIBN / CCl4 / 3 h / Heating 2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C 2.2: 87 percent / tetrabutylammonium iodide / tetrahydrofuran / 5 h / 20 °C 3.1: 89 percent / NaOH / ethanol / 12 h 4.1: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h 5.1: 82 percent / PdCl2(dppf) / dioxane / 3 h / 90 °C 6.1: 95 percent / HCl / tetrahydrofuran / 3 h / Heating 7.1: 100 percent / K2CO3 / propan-2-ol; CH2Cl2 / 5 h / 45 °C 8.1: 87 percent / AlCl3; NaCl / 0.08 h / 150 °C 9.1: 69 percent View Scheme

1: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h 2: 82 percent / PdCl2(dppf) / dioxane / 3 h / 90 °C 3: 95 percent / HCl / tetrahydrofuran / 3 h / Heating 4: 100 percent / K2CO3 / propan-2-ol; CH2Cl2 / 5 h / 45 °C 5: 87 percent / AlCl3; NaCl / 0.08 h / 150 °C 6: 69 percent View Scheme

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C 1.2: 87 percent / tetrabutylammonium iodide / tetrahydrofuran / 5 h / 20 °C 2.1: 89 percent / NaOH / ethanol / 12 h 3.1: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h 4.1: 82 percent / PdCl2(dppf) / dioxane / 3 h / 90 °C 5.1: 95 percent / HCl / tetrahydrofuran / 3 h / Heating 6.1: 100 percent / K2CO3 / propan-2-ol; CH2Cl2 / 5 h / 45 °C 7.1: 87 percent / AlCl3; NaCl / 0.08 h / 150 °C 8.1: 69 percent View Scheme

1: 82 percent / PdCl2(dppf) / dioxane / 3 h / 90 °C 2: 95 percent / HCl / tetrahydrofuran / 3 h / Heating 3: 100 percent / K2CO3 / propan-2-ol; CH2Cl2 / 5 h / 45 °C 4: 87 percent / AlCl3; NaCl / 0.08 h / 150 °C 5: 69 percent View Scheme

1: 89 percent / NaOH / ethanol / 12 h 2: 93 percent / 2,6-lutidine / CH2Cl2 / 1 h 3: 82 percent / PdCl2(dppf) / dioxane / 3 h / 90 °C 4: 95 percent / HCl / tetrahydrofuran / 3 h / Heating 5: 100 percent / K2CO3 / propan-2-ol; CH2Cl2 / 5 h / 45 °C 6: 87 percent / AlCl3; NaCl / 0.08 h / 150 °C 7: 69 percent View Scheme