Multi-step reaction with 9 steps
1: 98 percent / K2CO3 / acetone / 16 h / Heating
2: 1.) NaH / 1.) THF, reflux, 2 h, 2.) THF, RT, 1 h
3: 95 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h
4: 82 percent / pyridine / 0 - 20 °C
5: 53 percent / palladium(II) acetate, tri-o-tolylphosphine, K2CO3, tetrabutylammonium iodide / dimethylformamide / 1.5 h / 120 °C
6: H2S(g), pyridine, Et3N / 48 h / Ambient temperature
7: ethanol / 1 h / Heating
8: NH4OAc / methanol / 2 h / 60 °C
9: aq. K2CO3 / tetrahydrofuran / 2 h / Ambient temperature
With
pyridine; hydrogen sulfide; ammonium acetate; hydrogen; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm9701076