hydrogen; palladium dihydroxide in methanol

Multi-step reaction with 7 steps 1: hydrogen / Pd/CaCO3 / ethyl acetate2: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C3: hydrazine / ethanol / 6 h / Heating4: Et3N / CH2Cl2 5: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C6: Et3N / CH2Cl2 7: K2CO3 / methanol  

With  potassium carbonate in  methanol  

Multi-step reaction with 4 steps 1: Et3N / CH2Cl2 2: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C3: Et3N / CH2Cl2 4: K2CO3 / methanol  

Multi-step reaction with 3 steps 1: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C2: Et3N / CH2Cl2 3: K2CO3 / methanol  

Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: K2CO3 / methanol  

Multi-step reaction with 5 steps 1: hydrazine / ethanol / 6 h / Heating2: Et3N / CH2Cl2 3: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C4: Et3N / CH2Cl2 5: K2CO3 / methanol