1.1: 93 percent / EDC*HCl; DMAP; DIPEA / CH2Cl2 2.1: 95 percent / NaH / tetrahydrofuran 3.1: 87 percent / Bu3SnH; AcOH / (Ph3P)2PdCl2 / CH2Cl2 4.1: 86 percent / (PhSeO)2O / CH2Cl2 5.1: DMSO; Tf2O / CH2Cl2 5.2: DIPEA; t-BuOH; tert-butyl-tetramethylguanidine / CH2Cl2 5.3: 55 percent / CH2Cl2 6.1: 85 percent / p-TsOH / CHCl3 7.1: 55 percent / N-methylpyridinium-4-carboxaldehyde iodide; DBU; oxalic acid 8.1: 91 percent / silica gel / ethanol 9.1: 88 percent / AgNO3 / acetonitrile; H2O View Scheme

1.1: 95 percent / NaH / tetrahydrofuran 2.1: 87 percent / Bu3SnH; AcOH / (Ph3P)2PdCl2 / CH2Cl2 3.1: 86 percent / (PhSeO)2O / CH2Cl2 4.1: DMSO; Tf2O / CH2Cl2 4.2: DIPEA; t-BuOH; tert-butyl-tetramethylguanidine / CH2Cl2 4.3: 55 percent / CH2Cl2 5.1: 85 percent / p-TsOH / CHCl3 6.1: 55 percent / N-methylpyridinium-4-carboxaldehyde iodide; DBU; oxalic acid 7.1: 91 percent / silica gel / ethanol 8.1: 88 percent / AgNO3 / acetonitrile; H2O View Scheme

1.1: 87 percent / Bu3SnH; AcOH / (Ph3P)2PdCl2 / CH2Cl2 2.1: 86 percent / (PhSeO)2O / CH2Cl2 3.1: DMSO; Tf2O / CH2Cl2 3.2: DIPEA; t-BuOH; tert-butyl-tetramethylguanidine / CH2Cl2 3.3: 55 percent / CH2Cl2 4.1: 85 percent / p-TsOH / CHCl3 5.1: 55 percent / N-methylpyridinium-4-carboxaldehyde iodide; DBU; oxalic acid 6.1: 91 percent / silica gel / ethanol 7.1: 88 percent / AgNO3 / acetonitrile; H2O View Scheme

1.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 23 °C 2.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 23 °C 3.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 23 °C 4.1: oxygen / palladium 10 on activated carbon / methanol / 24 h / 23 °C 5.1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h / 23 °C 6.1: 2,4,6-trimethyl-pyridine; lithium iodide / 24 h / 23 °C 7.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 7.2: 20 h / 23 - 70 °C 8.1: benzeneseleninic anhydride / dichloromethane 9.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 10.1: methanesulfonic acid / dichloromethane 11.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 12.1: ethanol 13.1: water; silver nitrate / acetonitrile View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 23 °C 2.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 23 °C 3.1: oxygen / palladium 10 on activated carbon / methanol / 24 h / 23 °C 4.1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h / 23 °C 5.1: 2,4,6-trimethyl-pyridine; lithium iodide / 24 h / 23 °C 6.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 6.2: 20 h / 23 - 70 °C 7.1: benzeneseleninic anhydride / dichloromethane 8.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 9.1: methanesulfonic acid / dichloromethane 10.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 11.1: ethanol 12.1: water; silver nitrate / acetonitrile View Scheme

1.1: dichloromethane / 2 h / 23 °C 2.1: chloro-trimethyl-silane; methanol / 1.5 h / 23 °C 3.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 19 h / 23 °C 4.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C 5.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 23 °C 6.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.75 h / 23 °C 7.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 7.2: 20 h / 23 - 70 °C 8.1: benzeneseleninic anhydride / dichloromethane 9.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 10.1: methanesulfonic acid / dichloromethane 11.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 12.1: ethanol 13.1: water; silver nitrate / acetonitrile View Scheme

1.1: chloro-trimethyl-silane; methanol / 1.5 h / 23 °C 2.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 19 h / 23 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C 4.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 23 °C 5.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.75 h / 23 °C 6.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 6.2: 20 h / 23 - 70 °C 7.1: benzeneseleninic anhydride / dichloromethane 8.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 9.1: methanesulfonic acid / dichloromethane 10.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 11.1: ethanol 12.1: water; silver nitrate / acetonitrile View Scheme

1.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 19 h / 23 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C 3.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 23 °C 4.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.75 h / 23 °C 5.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 5.2: 20 h / 23 - 70 °C 6.1: benzeneseleninic anhydride / dichloromethane 7.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 8.1: methanesulfonic acid / dichloromethane 9.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 10.1: ethanol 11.1: water; silver nitrate / acetonitrile View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C 2.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 23 °C 3.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.75 h / 23 °C 4.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 4.2: 20 h / 23 - 70 °C 5.1: benzeneseleninic anhydride / dichloromethane 6.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 7.1: methanesulfonic acid / dichloromethane 8.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 9.1: ethanol 10.1: water; silver nitrate / acetonitrile View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 23 °C 2.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.75 h / 23 °C 3.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 3.2: 20 h / 23 - 70 °C 4.1: benzeneseleninic anhydride / dichloromethane 5.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 6.1: methanesulfonic acid / dichloromethane 7.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 8.1: ethanol 9.1: water; silver nitrate / acetonitrile View Scheme