Multi-step reaction with 9 steps
1: 81.5 percent / imidazole / dimethylformamide / 3 h / Ambient temperature
2: FeCl3*6H2O, C, NH2-NH2*H2O / methanol; H2O / 5 h / 70 °C
3: 89.3 percent / Et3N / CH2Cl2 / 1.5 h / 0 - 20 °C
4: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h
5: 92.6 percent / NH2-NH2*H2O / ethanol / 1 h / Heating
6: WSCD*HCl, HOBt / dimethylformamide / 2 h / Ambient temperature
7: 81 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
8: 69.3 percent / PPh3, CBr4 / CH2Cl2 / 3 h / Ambient temperature
9: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h
With
1H-imidazole; carbon tetrabromide; WSCD*HCl; tetrabutyl ammonium fluoride; iron(III) chloride; sodium hydride; benzotriazol-1-ol; hydrazine hydrate; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm980300f