hydrogen; palladium 10 on activated carbon in ethanol T=20°C; P=3102.97 Torr; 6 h;

sodium hydroxide in ethanol 6 h; Heating;

1: p-TsOH / 3 h / 0 - 10 °C 2: 1.) LiN(iPr)2, 2.) HMPA / 1.) THF, -70 deg C, 10 min, 2.) THF, a) -70 deg C, 7 h, b) 90 deg C, 16 h 3: aq. H2SO4 4: pyridine 5: LiBr / dimethylsulfoxide / 1.5 h / 70 °C 6: 1.) n-BuLi, 2.) HMPA / 1.) THF, from 5 deg C to 10 deg C, 1 h, 2.) THF, 19 h 7: aq. H2SO4 8: PBr3, pyridine / diethyl ether 9: 1.) EtMgBr, 2.) CuI / 1.) THF, 40 deg C, 30 min, 2.) THF, a) 50 deg C, 3 h, b) RT, overnight 10: H2, quinoline / Pd/BaSO4 / ethyl acetate 11: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 1.) LiN(iPr)2, 2.) HMPA / 1.) THF, -70 deg C, 10 min, 2.) THF, a) -70 deg C, 7 h, b) 90 deg C, 16 h 2: aq. H2SO4 3: pyridine 4: LiBr / dimethylsulfoxide / 1.5 h / 70 °C 5: 1.) n-BuLi, 2.) HMPA / 1.) THF, from 5 deg C to 10 deg C, 1 h, 2.) THF, 19 h 6: aq. H2SO4 7: PBr3, pyridine / diethyl ether 8: 1.) EtMgBr, 2.) CuI / 1.) THF, 40 deg C, 30 min, 2.) THF, a) 50 deg C, 3 h, b) RT, overnight 9: H2, quinoline / Pd/BaSO4 / ethyl acetate 10: lithium t-butyl thiolate / dimethylformamide View Scheme

1: pyridine 2: LiBr / dimethylsulfoxide / 1.5 h / 70 °C 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, from 5 deg C to 10 deg C, 1 h, 2.) THF, 19 h 4: aq. H2SO4 5: PBr3, pyridine / diethyl ether 6: 1.) EtMgBr, 2.) CuI / 1.) THF, 40 deg C, 30 min, 2.) THF, a) 50 deg C, 3 h, b) RT, overnight 7: H2, quinoline / Pd/BaSO4 / ethyl acetate 8: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 1.) EtMgBr, 2.) CuI / 1.) THF, 40 deg C, 30 min, 2.) THF, a) 50 deg C, 3 h, b) RT, overnight 2: H2, quinoline / Pd/BaSO4 / ethyl acetate 3: lithium t-butyl thiolate / dimethylformamide View Scheme

1: H2N(CH2)2NH2 / dimethylsulfoxide / 2 h / 8 - 10 °C 2: 1.) EtMgBr, 2.) CuCl / 1.) THF, from 50 deg C to 60 deg C, 1 h, 2.) THF, 60 deg C, 1 h 3: HCl, MeOH 4: pyridine 5: NaI, Me3SiCl / acetonitrile 6: 1.) LiN(i-Pr)2, 2.) HMPA 7: H2, quinoline / Pd/BaSO4 / ethyl acetate 8: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 99 percent / imidazole / dimethylformamide / 12 h / 35 °C 2: 1.) EtMgBr, 2.) CuCl / 1.) THF, 40 deg C, 2.) THF, from 50 deg C to 55 deg C, 2 h 3: 52 percent / Bu4NF / tetrahydrofuran / 12 h 4: pyridine 5: NaI, Me3SiCl / acetonitrile 6: 1.) LiN(i-Pr)2, 2.) HMPA 7: H2, quinoline / Pd/BaSO4 / ethyl acetate 8: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 1.) LiN(i-Pr)2, 2.) HMPA 2: H2, quinoline / Pd/BaSO4 / ethyl acetate 3: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 1.) EtMgBr, 2.) CuCl / 1.) THF, 40 deg C, 2.) THF, from 50 deg C to 55 deg C, 2 h 2: 52 percent / Bu4NF / tetrahydrofuran / 12 h 3: pyridine 4: NaI, Me3SiCl / acetonitrile 5: 1.) LiN(i-Pr)2, 2.) HMPA 6: H2, quinoline / Pd/BaSO4 / ethyl acetate 7: lithium t-butyl thiolate / dimethylformamide View Scheme