1.1: hydrogen / palladium 10 on activated carbon / N,N-dimethyl-formamide / 2 h / 23 °C 1.2: 4 h / 23 °C 2.1: chloro-trimethyl-silane; methanol / 6 h / 70 °C 3.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 23 °C 4.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 23 °C 5.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 23 °C 6.1: oxygen / palladium 10 on activated carbon / methanol / 24 h / 23 °C 7.1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h / 23 °C 8.1: 2,4,6-trimethyl-pyridine; lithium iodide / 24 h / 23 °C 9.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 9.2: 20 h / 23 - 70 °C 10.1: benzeneseleninic anhydride / dichloromethane 11.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 12.1: methanesulfonic acid / dichloromethane 13.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 14.1: ethanol 15.1: water; silver nitrate / acetonitrile View Scheme

1.1: chloro-trimethyl-silane; methanol / 6 h / 70 °C 2.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 23 °C 3.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 23 °C 4.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 23 °C 5.1: oxygen / palladium 10 on activated carbon / methanol / 24 h / 23 °C 6.1: N-ethyl-N,N-diisopropylamine / 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h / 23 °C 7.1: 2,4,6-trimethyl-pyridine; lithium iodide / 24 h / 23 °C 8.1: hydrogen / palladium 10 on activated carbon / acetonitrile / 2.5 h / 23 °C 8.2: 20 h / 23 - 70 °C 9.1: benzeneseleninic anhydride / dichloromethane 10.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol 11.1: methanesulfonic acid / dichloromethane 12.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 13.1: ethanol 14.1: water; silver nitrate / acetonitrile View Scheme

1: 91 percent / benzeneseleninic anhydride / CH2Cl2 / 0.08 h / -10 °C 2: 58 percent View Scheme

1: 85 percent / p-TsOH / CHCl3 2: 55 percent / N-methylpyridinium-4-carboxaldehyde iodide; DBU; oxalic acid 3: 91 percent / silica gel / ethanol 4: 88 percent / AgNO3 / acetonitrile; H2O View Scheme

1.1: DMSO; Tf2O / CH2Cl2 1.2: DIPEA; t-BuOH; tert-butyl-tetramethylguanidine / CH2Cl2 1.3: 55 percent / CH2Cl2 2.1: 85 percent / p-TsOH / CHCl3 3.1: 55 percent / N-methylpyridinium-4-carboxaldehyde iodide; DBU; oxalic acid 4.1: 91 percent / silica gel / ethanol 5.1: 88 percent / AgNO3 / acetonitrile; H2O View Scheme

1.1: 86 percent / (PhSeO)2O / CH2Cl2 2.1: DMSO; Tf2O / CH2Cl2 2.2: DIPEA; t-BuOH; tert-butyl-tetramethylguanidine / CH2Cl2 2.3: 55 percent / CH2Cl2 3.1: 85 percent / p-TsOH / CHCl3 4.1: 55 percent / N-methylpyridinium-4-carboxaldehyde iodide; DBU; oxalic acid 5.1: 91 percent / silica gel / ethanol 6.1: 88 percent / AgNO3 / acetonitrile; H2O View Scheme

1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide 2: ethanol 3: water; silver nitrate / acetonitrile View Scheme

1: 58 percent View Scheme

Multistep reaction.;