Multi-step reaction with 13 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C
1.2: 87.6 percent / tetrahydrofuran / 24 h / 40 °C
2.1: 73.5 percent / LiBH4 / tetrahydrofuran / 1 h / 20 °C
3.1: 96.8 percent / pyridine / 0.5 h / 20 °C
4.1: 100 percent / PdCl2(PPh3)2; Et3N; CuI / tetrahydrofuran / 18 h / 20 °C
5.1: 77.3 percent / H2 / 10 percent Pd/C / ethanol / 20 °C / 760 Torr
6.1: 85.8 percent / benzyltrimethylammonium dichloroiodate; CaCO3 / CH2Cl2 / 2.5 h / 20 °C
7.1: Ac2O / 2 h / 50 °C
7.2: 90 percent / tetrahydrofuran / 0.5 h / 0 °C
8.1: 68.2 percent / PdCl2(PPh3)2; Et3N; CuI / tetrahydrofuran / 44 h / 20 °C
9.1: 77.3 percent / H2 / 10 percent Pd/C / ethanol / 1 h / 20 °C / 760 Torr
10.1: BH3 / tetrahydrofuran / 1 h / 0 °C
11.1: 910 mg / aq. NaOH / methanol / 0.33 h / 20 °C
12.1: 73.6 percent / 2,6-lutidine / 1,2-dichloro-ethane / 0.75 h / Heating
13.1: 95.7 percent / imidazole / dimethylformamide / 0 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; lithium borohydride; borane; hydrogen; acetic anhydride; sodium hydride; N,N,N-trimethylbenzenemethanaminium dichloroiodate; triethylamine; calcium carbonate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
4.1: Sonogashira coupling / 8.1: Sonogashira coupling;
DOI:10.1016/S0040-4020(02)00099-6