1: With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; potassium carbonate in N,N-dimethyl-formamide T=80°C; 2: With hydrogenchloride in N,N-dimethyl-formamide 1 h;

1: With potassium carbonate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane in DMF (N,N-dimethyl-formamide); water T=80°C; 2: With hydrogenchloride in DMF (N,N-dimethyl-formamide); water 1 h;

1.1: 4.0 g / tetrahydrofuran / 18 h / 20 °C 2.1: Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; aq. K2CO3 / dimethylformamide / 80 °C 2.2: 42 percent / aq. HCl / dimethylformamide / 1 h View Scheme

1.1: SOCl2 / CH2Cl2 / 2 h / 20 °C 2.1: 4.0 g / tetrahydrofuran / 18 h / 20 °C 3.1: Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; aq. K2CO3 / dimethylformamide / 80 °C 3.2: 42 percent / aq. HCl / dimethylformamide / 1 h View Scheme

1.1: 64 percent / NaBH4 / aq. ethanol 2.1: SOCl2 / CH2Cl2 / 2 h / 20 °C 3.1: 4.0 g / tetrahydrofuran / 18 h / 20 °C 4.1: Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; aq. K2CO3 / dimethylformamide / 80 °C 4.2: 42 percent / aq. HCl / dimethylformamide / 1 h View Scheme