Multi-step reaction with 9 steps
1: xylene / 3 h / 105 °C
2: SnCl2*2H2O, conc. HCl, AcOH / Ambient temperature
3: (i-Pr)2NEt / tetrahydrofuran / Ambient temperature
4: 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: (Ph3P)2PdCl2, Et3N, 2,6-di-tert-butyl-4-methylphenol / dimethylformamide / 3 h / 125 °C
9: H2 / PtO2 / ethyl acetate / 48 h / 60 °C / 7757.2 Torr
With
hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; hydrogen; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; tin(ll) chloride; sodium nitrite;
platinum(IV) oxide;
In
tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; xylene;
DOI:10.1021/jm9707028