Multi-step reaction with 10 steps
1.1: hydrogenchloride; zinc / water / Inert atmosphere
2.1: sodium hydroxide / Inert atmosphere
2.2: Inert atmosphere; Reflux
3.1: 1H-imidazole / dichloromethane / 25 °C / Inert atmosphere
4.1: ytterbium(III) triflate / acetonitrile / 3 h / 130 °C / Microwave irradiation; Inert atmosphere
5.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / 40 °C / Inert atmosphere
6.1: indium(III) chloride / dichloromethane / 12 h / 25 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere
8.1: sodium hydride / tetrahydrofuran; mineral oil / 12 h / 25 °C / Inert atmosphere
9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere
10.1: lithium hexamethyldisilazane / 1 h / -78 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; indium(III) chloride; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; lithium hexamethyldisilazane; ytterbium(III) triflate; zinc; diethylazodicarboxylate;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
5.1: |Mitsunobu Displacement;
DOI:10.1021/jm401767k