Multi-step reaction with 13 steps
1.1: pyridine / 1 h / 0 °C
2.1: 0.878 g / TFA / H2O / 0.33 h / 20 °C
3.1: Bu2SnO / benzene; methanol / 1.5 h / 60 °C
3.2: 88 percent / toluene / 2 h / 65 °C
4.1: H2SO4; AcOH / 0.5 h / 20 °C
5.1: 0.858 g / hydrazine acetate / dimethylformamide / 0.67 h / 20 °C
6.1: 72 percent / DBU / CH2Cl2 / 1 h / 0 °C
7.1: 86 percent / BF3*OEt2 / CH2Cl2 / 2.5 h / -50 °C
8.1: PdCl2 / CH2Cl2 / 4 h / 20 °C
9.1: pyridine / 20 °C
10.1: 0.278 g / hydrazine acetate / methanol; CH2Cl2 / 4 h / 20 °C
11.1: 71 percent / TMSOTf / CH2Cl2 / 3 h / -50 °C
12.1: 92 percent / PdCl2 / methanol; CH2Cl2 / 7 h / 20 °C
13.1: 70 percent / TMSOTf / CH2Cl2 / 1.5 h / -50 °C
With
pyridine; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; boron trifluoride diethyl etherate; hydrazinium monoacetate; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium dichloride;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.carres.2004.06.010