Multi-step reaction with 7 steps
1.1: N-Bromosuccinimide / tetrahydrofuran / 3 h / 0 - 25 °C
2.1: trifluoroacetic acid; dihydrogen peroxide / dichloromethane / 1.67 h / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C
3.2: 18 h / 80 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
5.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 1 h / 120 °C / Microwave irradiation
6.1: boron tribromide / dichloromethane; n-heptane / 1.67 h / 0 °C
7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h
7.2: 6 h / 20 °C
With
bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; lithium aluminium tetrahydride; dihydrogen peroxide; boron tribromide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; n-heptane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
5.1: |Heck Reaction;
DOI:10.1021/acs.jmedchem.7b01682