Multi-step reaction with 10 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 3 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
2.2: 6 h / 20 °C
3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / methanol; water; toluene / 10 h / Inert atmosphere; Reflux
4.1: sodium hydroxide / tetrahydrofuran; ethanol; water / 3 h / Reflux
5.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C
6.1: sodium tetrahydroborate / tetrahydrofuran; 1,2-dimethoxyethane / 1 h / 0 °C
7.1: thionyl chloride / toluene / 2 h / Reflux
8.1: N,N-dimethyl-formamide / 6 h / 20 °C
9.1: hydrazine hydrate / ethanol / 1 h / Reflux
10.1: tetrahydrofuran / 1 h / 20 °C
With
sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; oxalyl dichloride; sodium hydride; sodium carbonate; hydrazine hydrate; N,N-dimethyl-formamide; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; toluene;
3.1: Suzuki coupling;
DOI:10.1016/j.bmc.2011.06.059