Multi-step reaction with 12 steps
1.1: sodium hydrogensulfite / methanol; water / 12 h / 60 °C
2.1: hydrogen bromide / 2 h / 150 °C
3.1: sodium hydroxide / 17 h / 20 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
4.2: 1.5 h / -78 - 20 °C
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C
5.2: 2 h / 20 °C
6.1: trifluorormethanesulfonic acid / dichloromethane / 48 h / 20 °C
7.1: hydrazine hydrate / ethanol / 12 h / Reflux
8.1: acetic acid / ethanol / 7 h / Reflux
9.1: bromine; acetic acid / 12 h / 50 °C
10.1: pyridine / water / 12 h / 20 °C
11.1: trichlorophosphate / 6 h / 80 °C
11.2: Cooling with ice
12.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane / 1 h / 80 °C
With
pyridine; tetrakis(triphenylphosphine) palladium(0); trifluorormethanesulfonic acid; hydrogen bromide; bromine; sodium hydride; sodium carbonate; hydrazine hydrate; sodium hydrogensulfite; acetic acid; sodium hydroxide; lithium hexamethyldisilazane; trichlorophosphate;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; mineral oil;
DOI:10.1016/j.bmc.2011.11.015