Multi-step reaction with 7 steps
1: 74 percent / tert-BuOK / 2-methyl-propan-2-ol; dimethylformamide / 15 h / Ambient temperature
2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT, 1 h
3: NH2NH2*H2O / dimethylformamide / 1 h / Ambient temperature
4: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 1 h
5: H2SO4, TFA / 14 h / Ambient temperature
6: 76 percent / H2 / 20percent Pd/C / ethanol / 14 h / 80 °C / 2660 Torr
7: 78 percent / Et3N, 4-dimethylaminopyridine / CH2Cl2 / 1 h / Ambient temperature
With
dmap; sulfuric acid; potassium tert-butylate; hydrogen; sodium hydride; hydrazine hydrate; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1248/cpb.40.2620