potassium carbonate in N,N-dimethyl-formamide 18 h; Ambient temperature;

potassium carbonate in DMF (N,N-dimethyl-formamide) T=20°C; 18 h;

potassium carbonate; tetraethylammonium bromide in N,N-dimethyl-formamide T=60 - 70°C; 6 h;

potassium carbonate in N-methyl-acetamide; chloroform

tetraethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate in acetonitrile T=70°C; 1 h;

1.1: 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 2.1: hydrogen; K2CO3 / Pd-C / H2O; methanol; 1-methyl-pyrrolidin-2-one / 21.5 h / 45 °C / 760 Torr 2.2: 2.58 g / NaOH / H2O / 2 h / 50 °C / pH 13.0 3.1: 91 percent / 4-(dimethylamino)pyridine / dimethylformamide / 1.5 h / 45 °C 4.1: 70 percent / tetraethylammonium chloride; N,N-dimethylaniline; phosphorus oxychloride / acetonitrile / 1 h / 70 °C View Scheme

1.1: sodium acetate / 4 h / 70 °C 2.1: sodium bromide; HCl / dimethylformamide / 8 h / 70 °C 3.1: 15.1 g / HCl / dimethylformamide / 3 h / 40 °C 4.1: 95.7 percent / AcOH; p-TsOH*H2O / 3 h / 105 °C 5.1: 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 6.1: hydrogen; K2CO3 / Pd-C / H2O; methanol; 1-methyl-pyrrolidin-2-one / 21.5 h / 45 °C / 760 Torr 6.2: 2.58 g / NaOH / H2O / 2 h / 50 °C / pH 13.0 7.1: 91 percent / 4-(dimethylamino)pyridine / dimethylformamide / 1.5 h / 45 °C 8.1: 70 percent / tetraethylammonium chloride; N,N-dimethylaniline; phosphorus oxychloride / acetonitrile / 1 h / 70 °C View Scheme

1.1: sodium bromide; HCl / dimethylformamide / 8 h / 70 °C 2.1: 15.1 g / HCl / dimethylformamide / 3 h / 40 °C 3.1: 95.7 percent / AcOH; p-TsOH*H2O / 3 h / 105 °C 4.1: 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 5.1: hydrogen; K2CO3 / Pd-C / H2O; methanol; 1-methyl-pyrrolidin-2-one / 21.5 h / 45 °C / 760 Torr 5.2: 2.58 g / NaOH / H2O / 2 h / 50 °C / pH 13.0 6.1: 91 percent / 4-(dimethylamino)pyridine / dimethylformamide / 1.5 h / 45 °C 7.1: 70 percent / tetraethylammonium chloride; N,N-dimethylaniline; phosphorus oxychloride / acetonitrile / 1 h / 70 °C View Scheme

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane 2 h; Heating;

1: 94 percent / pyridine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 1 h / 0 °C 2: H2 / 10percent Pd/C / ethanol / 18 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / -5 °C 4: NaI / acetone / 2 h / Heating 5: 75 percent / K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme