1: 97 percent / 1,1,3,3-tetramethylguanidine / CH2Cl2 / 48 h / 23 °C 2: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 3: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C 4: 89 percent / aq. KOH / methanol / 1 h / Heating 5: SOCl2; DMF / toluene / 0.33 h / 70 °C View Scheme

1: 87 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 0 °C 2: 97 percent / 1,1,3,3-tetramethylguanidine / CH2Cl2 / 48 h / 23 °C 3: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 4: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C 5: 89 percent / aq. KOH / methanol / 1 h / Heating 6: SOCl2; DMF / toluene / 0.33 h / 70 °C View Scheme

1: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C 2: 89 percent / aq. KOH / methanol / 1 h / Heating 3: SOCl2; DMF / toluene / 0.33 h / 70 °C View Scheme