Multi-step reaction with 13 steps
1: NEt3 / tetrahydrofuran; diethyl ether / 0.75 h / 0 - 20 °C
2: NaOH / methanol / 50 °C
3: PyBOP; NEt3 / CH2Cl2 / 15 h / 20 °C
4: 69 percent / t-BuLi; I2 / tetrahydrofuran / -78 - -10 °C
5: 78 percent / H2SO4 / H2O / 3.5 h / 95 °C
6: 62 percent / LiCl; Na2CO3 / Pd(dppf)Cl2*CH2Cl2 / dimethylformamide / 15 h / 100 °C
7: 98 percent / IPy2BF4; TfOH / CH2Cl2 / 1.5 h / 20 °C
8: 100 percent / Na2CO3 / Pd(dppf)Cl2*CH2Cl2 / ethanol; toluene / 15 h / 90 °C
9: 89 percent / DMAP; K2CO3 / CH2Cl2 / 1 h / 20 °C
10: 84 percent / H2 / Pd(OH)2/C / ethanol; acetic acid / 48 h / 20 °C / 2585.74 Torr
11: Zn(N3)2*2Py; PPh3; imidazole / DEAD / CH2Cl2 / 15 h / 20 °C
12: H2 / Pd(OH)2/C / ethanol / 1.5 h / 20 °C / 2585.74 Torr
13: 90 percent / NaHCO3 / CH2Cl2; H2O / 0.5 h / 20 °C
With
1H-imidazole; dmap; zinc azide * 2 pyridine; Barluenga reagent; trifluorormethanesulfonic acid; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; tert.-butyl lithium; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; triphenylphosphine; lithium chloride;
palladium dihydroxide; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene;
8: Suzuki-Miayura cross-coupling;
DOI:10.1016/S0040-4039(01)01322-3