trimethylsilyl bromide in acetonitrile 14 h; Ambient temperature;

With  hydrogen; palladium hydroxide - carbon in  ethanol; cyclohexane  Heating;   

Multi-step reaction with 3 steps 1: 97 percent / Et3N / CH2Cl2 2: 67 percent / cesium carbonate / dimethylformamide / 2 h / 90 °C3: 65 percent / H2 / Pd(OH)2 on carbon / ethanol; cyclohexane / Heating  

Multi-step reaction with 4 steps 1: 85 percent / 80 percent aq.acetic acid2: 97 percent / Et3N / CH2Cl2 3: 67 percent / cesium carbonate / dimethylformamide / 2 h / 90 °C4: 65 percent / H2 / Pd(OH)2 on carbon / ethanol; cyclohexane / Heating