1: 63 percent / n-BuLi / tetrahydrofuran / 1 h 2: POCl3 / pyridine / 1.) room temp, 1 h, 2:) 75 deg C, 1.5 h 3: NaBH4 / ethanol / 2 h 4: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 5: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 6: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 7: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 8: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 9: 58 percent / CH2Cl2 / 1 h / Ambient temperature 10: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 11: SOCl2 / 2 h / Ambient temperature 12: 60 percent / acetonitrile / 0.5 h / Heating 13: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: NaBH4 / ethanol / 2 h 2: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 3: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 4: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 5: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 6: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 7: 58 percent / CH2Cl2 / 1 h / Ambient temperature 8: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 9: SOCl2 / 2 h / Ambient temperature 10: 60 percent / acetonitrile / 0.5 h / Heating 11: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 8: SOCl2 / 2 h / Ambient temperature 9: 60 percent / acetonitrile / 0.5 h / Heating 10: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: POCl3 / pyridine / 1.) room temp, 1 h, 2:) 75 deg C, 1.5 h 2: NaBH4 / ethanol / 2 h 3: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 4: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 5: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 6: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 7: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 8: 58 percent / CH2Cl2 / 1 h / Ambient temperature 9: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 10: SOCl2 / 2 h / Ambient temperature 11: 60 percent / acetonitrile / 0.5 h / Heating 12: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 2: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 3: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 4: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 5: 58 percent / CH2Cl2 / 1 h / Ambient temperature 6: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 7: SOCl2 / 2 h / Ambient temperature 8: 60 percent / acetonitrile / 0.5 h / Heating 9: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 2: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 3: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 4: 58 percent / CH2Cl2 / 1 h / Ambient temperature 5: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 6: SOCl2 / 2 h / Ambient temperature 7: 60 percent / acetonitrile / 0.5 h / Heating 8: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 2: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 3: 58 percent / CH2Cl2 / 1 h / Ambient temperature 4: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 5: SOCl2 / 2 h / Ambient temperature 6: 60 percent / acetonitrile / 0.5 h / Heating 7: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

thionyl chloride 20 h; Ambient temperature;

1: SOCl2 / 2 h / Ambient temperature 2: 60 percent / acetonitrile / 0.5 h / Heating 3: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: 60 percent / acetonitrile / 0.5 h / Heating 2: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme