Multi-step reaction with 9 steps
1.1: 63 percent / NaOH / dioxane; H2O / 1 h / 20 °C
2.1: 80 percent / 1,2-dichloro-ethane / 3 h / 70 °C
3.1: 100 percent / K2CO3; 4-dimethylaminopyridine / tetrahydrofuran; H2O / 12 h / 20 °C
4.1: 82 percent / DEAD; Ph3P / CH2Cl2 / 3 h / 20 °C
5.1: aq. LiBH4 / tetrahydrofuran / 0 - 20 °C
5.2: Ac2O; DMAP / CH2Cl2 / 12 h / 20 °C
5.3: 47 percent / triethylsilane; TMSOTf; 2,6-lutidine / 12 h / 20 °C
6.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
7.1: 43 percent / Cs2CO3 / CH2Cl2 / 1 h / Heating
8.1: dppp; TEA; Pd(OAc)2 / dimethylformamide; H2O / 2.5 h / 70 °C
8.2: Cs2CO3; MeI / 0.75 h / 20 °C
8.3: aq. LiOH / tetrahydrofuran / 15 h / 20 °C
9.1: HATU; diisopropylethylamine / dimethylformamide / 15 h / 20 °C
With
dmap; palladium diacetate; sodium hydroxide; lithium borohydride; TEA; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2006.05.016