2,6-dimethylpyridine in N,N-dimethyl-formamide T=120°C; 5.5 h;

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C 2: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C 3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 5: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 6: 97 percent / tetrahydrofuran / 6 h / 20 °C 7: 90 percent / DMAP / 3 h / 80 °C 8: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 9: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 10: 76 percent / 48percent aq. HBr / 7 h / 120 °C 11: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 12: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 13: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C 2: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 3: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 4: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 5: 97 percent / tetrahydrofuran / 6 h / 20 °C 6: 90 percent / DMAP / 3 h / 80 °C 7: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 8: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 9: 76 percent / 48percent aq. HBr / 7 h / 120 °C 10: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 11: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 12: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 2: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 3: 97 percent / tetrahydrofuran / 6 h / 20 °C 4: 90 percent / DMAP / 3 h / 80 °C 5: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 6: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 7: 76 percent / 48percent aq. HBr / 7 h / 120 °C 8: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 9: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 10: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 2: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 3: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 4: 97 percent / tetrahydrofuran / 6 h / 20 °C 5: 90 percent / DMAP / 3 h / 80 °C 6: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 7: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 8: 76 percent / 48percent aq. HBr / 7 h / 120 °C 9: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 10: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 11: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 97 percent / tetrahydrofuran / 6 h / 20 °C 2: 90 percent / DMAP / 3 h / 80 °C 3: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 4: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 5: 76 percent / 48percent aq. HBr / 7 h / 120 °C 6: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 7: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 8: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 2: 97 percent / tetrahydrofuran / 6 h / 20 °C 3: 90 percent / DMAP / 3 h / 80 °C 4: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 5: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 6: 76 percent / 48percent aq. HBr / 7 h / 120 °C 7: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 8: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 9: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 2: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 3: 76 percent / 48percent aq. HBr / 7 h / 120 °C 4: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 5: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 6: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 90 percent / DMAP / 3 h / 80 °C 2: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 3: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 4: 76 percent / 48percent aq. HBr / 7 h / 120 °C 5: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 6: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 7: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 2: 76 percent / 48percent aq. HBr / 7 h / 120 °C 3: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 4: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 5: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme