n-butyllithium; N-methyl-N-(pyridin-2-yl)-formamide 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

n-butyllithium 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min 2: 98 percent / conc. HCl / aq. ethanol / 1.25 h / Heating 3: 91 percent / K2CO3 / dimethylformamide / 17 h / 80 °C 4: 96 percent / H2, NaOAc / 10percent Pd/C / methanol / 18 h 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, 30 min 6: DMAP / CH2Cl2 / 2 h / Ambient temperature 7: DBU / toluene / 3 h / 80 °C 8: 58 percent / 3.75 M aq. NaOH / aq. ethanol / 4 h View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min 2: 98 percent / conc. HCl / aq. ethanol / 1.25 h / Heating 3: 91 percent / K2CO3 / dimethylformamide / 17 h / 80 °C 4: 96 percent / H2, NaOAc / 10percent Pd/C / methanol / 18 h View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 30 min 2: 98 percent / conc. HCl / aq. ethanol / 1.25 h / Heating 3: 91 percent / K2CO3 / dimethylformamide / 17 h / 80 °C 4: 96 percent / H2, NaOAc / 10percent Pd/C / methanol / 18 h 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, 30 min 6: DMAP / CH2Cl2 / 2 h / Ambient temperature 7: DBU / toluene / 3 h / 80 °C View Scheme