Multi-step reaction with 8 steps
1.1: dibutyltin oxide / toluene / 3 h / Heating
1.2: 52 percent / tetrabutylammonium bromide / toluene / 3 h / Heating
2.1: pyridine / CH2Cl2 / 1 h / 0 °C
3.1: 0.42 g / sodium azide / dimethylformamide / 40 °C
4.1: 76 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH2Cl2 / 0 °C
5.1: 93 percent / hyrazine acetate / methanol; CH2Cl2 / 4 h / 20 °C
6.1: 51 percent / silver(I) oxide / dimethyl sulfide / tetrahydrofuran / 20 °C
7.1: 99 percent / 1,3-propanedithiol; triethylamine; pyridine / H2O / 20 °C
8.1: 63 percent / HATU; 1-hydroxy-7-azabenzotriazole; diisopropylethylamine / dimethylformamide / 4 h / 20 °C
With
pyridine; 1.3-propanedithiol; N-iodo-succinimide; sodium azide; 1-hydroxy-7-aza-benzotriazole; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrazinium monoacetate; di(n-butyl)tin oxide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; silver(l) oxide;
dimethylsulfide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.200601245