palladium diacetate Alkylation;

tetrabutylammomium bromide; sodium hydrogencarbonate; palladium diacetate in ethyl acetate; N,N-dimethyl-formamide

palladium diacetate; 4 Angstroem MS; tetrabutylammomium bromide; sodium carbonate in N,N-dimethyl-formamide T=60°C; 6 h;

1: With potassium chloride; tetra-n-butylammonium acetate; palladium diacetate; potassium carbonate in N,N-dimethyl-formamide T=90°C; Heck type coupling; 2: With hydrogenchloride in water

1.1: 68 percent / aq. NaOH / ethanol / 48 h / 38 °C 2.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 3.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 4.1: aq. NaOH / 2 h / 20 °C 4.2: aq. H2SO4 / 3 h / 0 °C 4.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 5.1: 4-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / dimethylformamide / 2 h / 20 °C 5.2: 62 percent / 4-methylmorpholine / dimethylformamide / 3.5 h / 20 °C View Scheme

1.1: 68 percent / aq. NaOH / ethanol / 48 h / 38 °C 2.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 3.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 4.1: aq. NaOH / 2 h / 20 °C 4.2: aq. H2SO4 / 3 h / 0 °C 4.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 View Scheme

1: With sodium tetrahydroborate in methanol; N,N-dimethyl-formamide T=0 - 5°C; 2: With water in methanol; N,N-dimethyl-formamide