Multi-step reaction with 9 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
1.2: 17 h / -78 - 20 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h
3.1: boron trifluoride diethyl etherate / 0.17 h / 20 °C / Inert atmosphere
3.2: 20 - 120 °C / Inert atmosphere
4.1: pyridine / dichloromethane / 1 h / 20 °C / Cooling with ice
5.1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / 1,2-dimethoxyethane; ethanol; water / 100 °C
6.1: sodium tetrahydroborate / methanol / 0.17 h / 20 °C
7.1: phosphorus tribromide / tetrahydrofuran; dichloromethane / 0.33 h / 20 °C / Inert atmosphere
8.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
9.1: methanol; sodium hydroxide / tetrahydrofuran / 0.17 h / 100 °C
With
pyridine; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; phosphorus tribromide; sodium hydrogencarbonate; potassium carbonate; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
5.1: Suzuki coupling;
DOI:10.1016/j.bmcl.2011.10.047