Multi-step reaction with 12 steps
1.1: trimethylaluminum / toluene / 110 °C
2.1: sodium hydrogencarbonate / 2 h / 20 °C
2.2: 1 h / 120 °C
3.1: palladium diacetate; triphenylphosphine; triethylamine / 20 h / 20 °C
4.1: cyclohexene; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 °C
4.2: 20 °C
5.1: N-Bromosuccinimide / acetonitrile / 8 h / 20 °C
6.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 18 h / 100 °C
7.1: boron trifluoride diethyl etherate / dichloromethane; cyclohexene / 3 h / 20 °C
8.1: lithium hydroxide / 1,4-dioxane; water / 3 h / 70 °C
9.1: hydrazine; 2-( 1H-7-azabenzotniazol-1-yl)-1,1,3,3-tetrarmethyluroniumhexafluorophosphate methanaminium; 4-methyl-morpholine / N,N-dimethyl-formamide / 2 h / 20 °C
10.1: sodium hydrogencarbonate / 1,4-dioxane; water / 6 h / 20 °C
11.1: hydrogenchloride / 1,4-dioxane / 72 h / 20 °C
12.1: triethylamine; dmap / N,N-dimethyl-formamide / 2 h / 20 °C
With
4-methyl-morpholine; hydrogenchloride; dmap; potassium phosphate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); 2-( 1H-7-azabenzotniazol-1-yl)-1,1,3,3-tetrarmethyluroniumhexafluorophosphate methanaminium; dimethylsulfide borane complex; boron trifluoride diethyl etherate; trimethylaluminum; palladium diacetate; sodium hydrogencarbonate; triethylamine; triphenylphosphine; lithium hydroxide; hydrazine; cyclohexene;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; cyclohexene;
3.1: |Sonogashira Cross-Coupling / 6.1: |Suzuki Coupling;
DOI:10.1016/j.bmcl.2014.03.039