1: 64 percent / pyridine / CH2Cl2 / 2 h 2: 39 percent / triflic acid / CH2Cl2; tetrahydrofuran / Ambient temperature 3: 34 percent / iodine monochloride / CH2Cl2 / Ambient temperature 4: 72 percent / 0.1 N NaOEt / 2 h / Ambient temperature 5: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened View Scheme

1: 37 percent / triflic acid / CH2Cl2; tetrahydrofuran / 0.83 h / Ambient temperature 2: 72 percent / 0.1 N NaOEt / 2 h / Ambient temperature 3: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened View Scheme

1: phosphorus oxychloride, 1-methylimidazole / acetonitrile / 0.5 h / Ambient temperature 2: triethylamine / 48 h / Ambient temperature 3: triethylamine / methanol / Ambient temperature 4: 66 percent / pyridine / 1 h / 100 °C 5: 62 percent / sodium hydride (60 percent) / tetrahydrofuran / 1.5 h / Ambient temperature 6: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened 7: NaI, trimethylsilyl chloride / acetonitrile / 2 h / Ambient temperature View Scheme

1: 66 percent / pyridine / 1 h / 100 °C 2: 62 percent / sodium hydride (60 percent) / tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened 4: NaI, trimethylsilyl chloride / acetonitrile / 2 h / Ambient temperature View Scheme

1: 37 percent / triflic acid / CH2Cl2; tetrahydrofuran / 0.83 h / Ambient temperature 2: 72 percent / 0.1 N NaOEt / 2 h / Ambient temperature 3: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened View Scheme

1: triethylamine / methanol / Ambient temperature 2: 66 percent / pyridine / 1 h / 100 °C 3: 62 percent / sodium hydride (60 percent) / tetrahydrofuran / 1.5 h / Ambient temperature 4: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened 5: NaI, trimethylsilyl chloride / acetonitrile / 2 h / Ambient temperature View Scheme

1: 34 percent / iodine monochloride / CH2Cl2 / Ambient temperature 2: 72 percent / 0.1 N NaOEt / 2 h / Ambient temperature 3: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened View Scheme

1: 62 percent / sodium hydride (60 percent) / tetrahydrofuran / 1.5 h / Ambient temperature 2: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened 3: NaI, trimethylsilyl chloride / acetonitrile / 2 h / Ambient temperature View Scheme

1: 1.) pyridine, DMF, copper powder, 4-dimethylaminopyridine / 1.) < -70 to 115 deg C; sealed tube, 2.) 8 h, 60 deg C; sealed tube was opened 2: NaI, trimethylsilyl chloride / acetonitrile / 2 h / Ambient temperature View Scheme

hydrogenchloride 2 h; Ambient temperature; Yield given;