Multi-step reaction with 8 steps
1: xylene / 3 h / 105 °C
2: 28 g / SnCl2*2H2O, conc. HCl, AcOH / Ambient temperature
3: 2.30 g / (i-Pr)2NEt / tetrahydrofuran / Ambient temperature
4: 0.93 g / xylene / 4 h / Heating
5: 1.) NaH / 1.) DMF, 1 h, 2.) DMF, RT, overnight
6: SnCl2*2H2O, conc. HCl, AcOH / Ambient temperature
7: 1.) NaNO2, H2SO4, 2.) NaI / 1.) water, 0 deg C, 20 min, 2.) water, from 0 deg C to RT
8: 0.1 g / (Ph3P)2PdCl2, Et3N / dimethylformamide / 19 h / 95 °C
With
hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sulfuric acid; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; tin(ll) chloride; sodium nitrite;
In
tetrahydrofuran; N,N-dimethyl-formamide; xylene;
DOI:10.1021/jm9707028