t-Bu Brett Phos; C44H62NO5PPdS; caesium carbonate in 1,4-dioxane T=50°C; 20 h; Sealed tubeInert atmosphere;

1: With hydroxylamine hydrochloride in methanol T=25°C; 4 h; 2: With pyridine; methanesulfonyl chloride T=25°C; 2 h;

triethylamine; trifluoroacetic anhydride in dichloromethane T=0°C; Dehydration; 302 h;

1: thionyl chloride / Heating 2: NH3(g) / 1,2-dichloro-ethane / -30 - 20 °C 3: trifluoroacetic anhydride; Et3N / CH2Cl2 / 302 h / 0 °C View Scheme

1.1: NaOMe / dimethylformamide / 0.5 h / 20 °C 1.2: 33 percent / NaOMe / dimethylformamide / 20 °C 2.1: 100 percent / NaOH; EtOH / 3 h / Heating 3.1: thionyl chloride / Heating 4.1: NH3(g) / 1,2-dichloro-ethane / -30 - 20 °C 5.1: trifluoroacetic anhydride; Et3N / CH2Cl2 / 302 h / 0 °C View Scheme

1: 100 percent / NaOH; EtOH / 3 h / Heating 2: thionyl chloride / Heating 3: NH3(g) / 1,2-dichloro-ethane / -30 - 20 °C 4: trifluoroacetic anhydride; Et3N / CH2Cl2 / 302 h / 0 °C View Scheme

1.1: N,N-dimethyl-formamide / 1 h / 63 - 68 °C 2.1: n-butyllithium / tetrahydrofuran / 0.42 h / -90 °C 2.2: 0.5 h / Cooling 3.1: hydroxylamine hydrochloride / methanol / 4 h / 25 °C 3.2: 2 h / 25 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.42 h / -90 °C 1.2: 0.5 h / Cooling 2.1: hydroxylamine hydrochloride / methanol / 4 h / 25 °C 2.2: 2 h / 25 °C View Scheme

pyridine hydrochloride T=200°C; 2 h;