Multi-step reaction with 10 steps
1.1: thionyl chloride / 0 - 60 °C
2.1: 4,4'-di-tert-butyl-2,2'-bipyridine / (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Inert atmosphere
3.1: copper dichloride / water; methanol / 90 °C
4.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 80 °C
5.1: toluene / 90 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 50 °C
7.1: hydrogen / platinum(IV) oxide / ethanol / 3620.13 Torr
8.1: sodium hydroxide; water / methanol / 1 h
9.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 16 h / 0 - 80 °C
10.1: trifluoroacetic acid / dichloromethane / 0.5 h / 5 - 20 °C
10.2: 4 - 6 °C
10.3: 5 °C
With
N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); diphenyl phosphoryl azide; water; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 4,4'-di-tert-butyl-2,2'-bipyridine; sodium hydroxide; copper dichloride;
platinum(IV) oxide; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; toluene; acetonitrile;