Multi-step reaction with 11 steps
1.1: triethylamine / tetrahydrofuran / 4 h / Heating
1.2: dimethylformamide / 18 h / 130 °C
2.1: KOH / methanol / 3 h / Heating
3.1: 3.3 g / HCl / 5 h / Heating
4.1: 74 percent / AlCl3 / CH2Cl2 / 20 °C
5.1: 96 percent / stannous chloride dihydrate / ethyl acetate / 0.5 h / Heating
6.1: 98 percent / Et2NH; CuI / Pd(PPh3)4 / 4 h / 20 °C
7.1: 61 percent / PdCl2(PhCN)2 / dimethylformamide / 0.5 h / 80 °C
8.1: 77 percent / CsF on Celite / acetonitrile / 24 h / Heating
9.1: 100 percent / NaOH / methanol / 4 h / Heating
10.1: 69 percent / HBTU; N-hydroxybenzotriazole; ethyldiisopropylamine / CH2Cl2 / 1.5 h / 20 °C
11.1: 61 percent / AcOH / 2,2,2-trifluoro-ethanol / 20 °C
With
hydrogenchloride; potassium hydroxide; sodium hydroxide; copper(l) iodide; aluminium trichloride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; tin(ll) chloride;
bis(benzonitrile)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; dichloromethane; 2,2,2-trifluoroethanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
4.1: Friedel-Crafts reaction;
DOI:10.1016/j.bmc.2005.08.018