Multi-step reaction with 9 steps
1.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C
2.1: methanesulfonic acid / toluene / 17 h / Reflux
3.1: palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl / tert-butyl alcohol / 15 h / 70 °C / Inert atmosphere
4.1: trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C
5.1: ammonia; hydrogen / tetrahydrofuran; methanol / 8 h / 70 °C / 3750.38 Torr
6.1: tetrahydrofuran / 3 h / 20 °C
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C
7.2: 0.5 h / 20 °C
8.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 6 h / 70 °C
9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 2 h / 20 °C
With
bis-triphenylphosphine-palladium(II) chloride; methanesulfonic acid; palladium 10% on activated carbon; ammonia; hydrogen; palladium diacetate; sodium hydride; 2,2'-bis(diphenylphosphino)biphenyl; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol;
8.1: Heck reaction;
DOI:10.1021/jm101236h