Multi-step reaction with 11 steps
1: 57 percent / K2CO3 / dimethylformamide / 12 h / 80 °C
2: aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C
3: K2CO3 / dimethylformamide / 12 h / 100 °C
4: AcOH / 1,2-dichloro-ethane / 4 h / 20 °C
5: Na(OAc)3BH / 1,2-dichloro-ethane / 12 °C
6: 84 percent / i-Pr2NEt / dimethylformamide / 12 h / 90 °C
7: 96 percent / Pd(PPh3)4; PhSiH3 / CH2Cl2 / 1 h / 20 °C
8: 69 percent / NaH / dimethylformamide / 12 h / 0 - 20 °C
9: Fe; aq. NH4Cl / ethanol / 1 h / 80 °C
10: pyridine / 1 h / 20 °C
11: 72 percent / NaOH / tetrahydrofuran; ethanol / 2.5 h / 20 °C
With
pyridine; sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); phenylsilane; sodium tris(acetoxy)borohydride; iron; sodium hydride; potassium carbonate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2004.06.023