Multi-step reaction with 13 steps
1.1: toluene-4-sulfonic acid / 2 h / 18 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C
2.2: 0.25 h
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 18 °C
3.2: 0.5 h / 0 - 18 °C
3.3: 0.5 h / 0 - 18 °C
4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2.5 h / Reflux
5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / tetrahydrofuran; water / 2 h / Reflux
6.1: acetic acid / water / 18 h / 50 °C
7.1: 1H-imidazole / N,N-dimethyl-formamide / 72 h
8.1: ammonia; hydrogen / methanol / 18 h / 18 °C
9.1: pyridine / dichloromethane / 0.25 h
10.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
10.2: 0.5 h / 18 °C
11.1: tetrakis(triphenylphosphine) palladium(0); dimedone / tetrahydrofuran / 1 h / 18 °C
12.1: N-chloro-succinimide / dichloromethane / 1 h / -78 - 18 °C
13.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 1.5 h
With
pyridine; 1H-imidazole; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 2,2'-azobis(isobutyronitrile); ammonia; hydrogen; tri-n-butyl-tin hydride; sodium hydride; dimedone; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; benzene;
5.1: Suzuki-Miyaura cross-coupling;
DOI:10.1021/jo201005d