Multi-step reaction with 7 steps
1.1: bromine / dichloromethane / 0 °C
2.1: potassium carbonate / acetone / 0 °C
3.1: water; lithium hydroxide / tetrahydrofuran
4.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / tetrahydrofuran
4.2: 20 °C
5.1: tetrahydrofuran; diethyl ether / 4 h / 20 °C
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / Reflux
7.1: palladium on activated charcoal; hydrogen / dichloromethane / 4 h / 20 °C
With
4-methyl-morpholine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; palladium on activated charcoal; water; hydrogen; bromine; potassium carbonate; lithium hydroxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;
DOI:10.1016/j.bmcl.2011.11.025