Multi-step reaction with 11 steps
1: pyridine / Ambient temperature
2: HBr(g), acetic acid / CH2Cl2 / 5 h / 0 °C
3: 1.) 4A molecular sieves, 2.) silver carbonate, silver perchlorate, 4A molecular sieves / 1.) CH2Cl2, RT, 6 h, 2.) CH2Cl2, 25 deg C, overnight
4: 100 percent / NaOCH3 / methanol
5: 1.) Drierite, 2.) p-toluenesulfonic acid monohydrate / 1.) DMF, RT, 2 h, 2.) DMF, 60 deg C, 12 h
6: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 3 h
7: 80percent aq. AcOH / 3 h / 50 °C
8: pyridine / CH2Cl2 / 4 h / Ambient temperature
9: 83 percent / H2, AcOH / 10percent Pd/C / ethanol / 24 h / 40 °C
10: 100 percent / pyridine / CH2Cl2 / 4 h / 45 °C
11: 100 percent / tributyltin hydride, α,α'-azobisisobutyronitrile / toluene / 2 h / 100 °C
With
pyridine; calcium sulfate; 4 A molecular sieve; azobisisobutyronitrile; hydrogen bromide; hydrogen; tri-n-butyl-tin hydride; sodium methylate; silver perchlorate; sodium hydride; toluene-4-sulfonic acid; acetic acid; silver carbonate;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; toluene;
DOI:10.1016/0008-6215(94)84107-1