Multi-step reaction with 11 steps
1.1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 2 h / 20 °C / Inert atmosphere
2.1: triphenylphosphine; 1H-imidazole; iodine / diethyl ether; acetonitrile / 12 h / 0 - 20 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C / Inert atmosphere
4.1: propionic acid; pyrrolidine / water; isopropyl alcohol / 18 h / 55 °C / Inert atmosphere
5.1: cerium(III) chloride heptahydrate / ethanol / 0.5 h / 0 °C / Inert atmosphere
5.2: 2 h / 0 °C / Inert atmosphere
6.1: 1H-imidazole / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere
7.2: 4 h / 20 °C / Inert atmosphere
8.1: Schwartz's reagent / benzene / 24 h / 20 °C / Inert atmosphere
8.2: 1 h
8.3: 20 h / 20 °C / Darkness
9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
9.2: 1 h / 20 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 16 h / 20 - 40 °C / Inert atmosphere
11.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere
With
pyrrolidine; pyridine; 1H-imidazole; Schwartz's reagent; chloro-trimethyl-silane; cerium(III) chloride heptahydrate; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; propionic acid; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; acetonitrile; mineral oil; pentane; benzene;
8.3: |Suzuki-Miyaura Coupling;
DOI:10.1002/anie.201400305