Multi-step reaction with 6 steps
1.1: conc. sulfuric acid / CH2Cl2
2.1: K2CO3 / acetone / Heating
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C
3.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C
3.3: 89 percent / aq. HCl / tetrahydrofuran; hexane
4.1: 78 percent / LiCl; aq. Na2CO3 / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating
5.1: 38 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / tetrahydrofuran / 25 h / 20 - 70 °C
6.1: 27 percent / H2SeO3 / dioxane; H2O / 1.5 h / Heating
With
n-butyllithium; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; selenious acid; sodium carbonate; potassium carbonate; lithium chloride;
tetrakis(triphenylphosphine) palladium(0); sulfuric acid;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; dichloromethane; water; acetone;
1.1: Friedel-Crafts alkylation / 4.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323