1.1: trifluoroacetic acid; triethylsilane / 4 h / 60 - 65 °C 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 25 - 35 °C 3.1: hydrogen; 5 palladium on charcoal / toluene / 24 h / 80 °C / 6000.6 Torr 3.2: |Reflux View Scheme

1.1: trifluoroacetic acid; triethylsilane / 4 h / 60 - 65 °C 1.2: 20 °C 2.1: sodium carbonate; 3,4,5-trimethoxyphenylboronic acid / water; o-xylene / 24 h / |Reflux 3.1: hydrogen; 5 palladium on charcoal / toluene / 24 h / 80 °C / 6000.6 Torr 4.1: hydrogenchloride / isopropyl alcohol / 5 h / pH < 2 4.2: pH 10 5.1: potassium hydroxide / methanol / 72 h / |Reflux View Scheme

1.1: trifluoroacetic acid; triethylsilane / 4 h / 60 - 65 °C 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 25 - 35 °C 3.1: hydrogen; 5 palladium on charcoal / toluene / 24 h / 80 °C / 6000.6 Torr 3.2: |Reflux View Scheme