1: 1-[5-(5-chlorothiophen-2-yl)isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine in dichloromethane T=20°C; 0.5 h; 2: 1-(1-methylethyl)-4-piperidinamine in dichloromethane T=20°C; 16 h;

1.1: t-BuOK / toluene / 0.17 h / 0 °C 1.2: toluene / 3 h / 20 °C 2.1: NH2OH*HCl / ethanol / 5 h / Heating 3.1: 16 g / NaBH4 / ethanol / 12 h / 20 °C 4.1: 77 percent / N-bromosuccinimide; PPh3(polystyrene-bound) / CH2Cl2 / 1 h / 20 °C 5.1: NaH / dimethylformamide / 0.5 h / 20 °C 5.2: dimethylformamide / 1 h / 80 °C 6.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 7.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 7.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 80 percent / Na(CN)BH3; AcOH / methanol / 16 h / 20 °C 2.1: 100 percent / HCl / methanol / 16 h / 20 °C 3.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 3.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: NaH / dimethylformamide / 0.5 h / 20 °C 1.2: dimethylformamide / 1 h / 80 °C 2.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 3.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 3.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 77 percent / N-bromosuccinimide; PPh3(polystyrene-bound) / CH2Cl2 / 1 h / 20 °C 2.1: NaH / dimethylformamide / 0.5 h / 20 °C 2.2: dimethylformamide / 1 h / 80 °C 3.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 4.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 4.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 16 g / NaBH4 / ethanol / 12 h / 20 °C 2.1: 77 percent / N-bromosuccinimide; PPh3(polystyrene-bound) / CH2Cl2 / 1 h / 20 °C 3.1: NaH / dimethylformamide / 0.5 h / 20 °C 3.2: dimethylformamide / 1 h / 80 °C 4.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 5.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 5.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: NH2OH*HCl / ethanol / 5 h / Heating 2.1: 16 g / NaBH4 / ethanol / 12 h / 20 °C 3.1: 77 percent / N-bromosuccinimide; PPh3(polystyrene-bound) / CH2Cl2 / 1 h / 20 °C 4.1: NaH / dimethylformamide / 0.5 h / 20 °C 4.2: dimethylformamide / 1 h / 80 °C 5.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 6.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 6.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 100 percent / HCl / methanol / 16 h / 20 °C 2.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 2.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 2.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 2.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme

1.1: HCl / 16 h / 20 °C 2.1: NaH / dimethylformamide / 0.5 h / 20 °C 2.2: dimethylformamide / 1 h / 80 °C 3.1: 253 mg / lithium hydroxide monohydrate / tetrahydrofuran / 2 h / 60 °C 4.1: Et3N; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 0.5 h / 20 °C 4.2: 60 percent / CH2Cl2 / 16 h / 20 °C View Scheme