1: 3-bromomethyliodobenzene With 1-ClCOOCH2CH2O-2-MeO-4-HOCOCH2-5-BzNHCH2-C6H2; caesium carbonate in N,N-dimethyl-formamide T=50°C; Esterification; 24 h; 2: (4-methoxyphenyl)-boronic acid With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=80°C; Arylation; Suzuki reaction; 20 h; 3: With penicillin G acylase in methanol T=37°C; Substitution; Product release; pH=7.0;

sodium carbonate in water; N,N-dimethyl-formamide T=90°C; Suzuki cross-coupling reaction; 0.5 h;

sodium carbonate in water; N,N-dimethyl-formamide T=90°C; Suzuki cross-coupling reaction; 0.5 h;

1: 3-iodo-benzyl alcohol With 4-(N,N-dimethlyamino)pyridine; polystyrene siloxane resin; triethylamine in dichloromethane T=20°C; 1 h; 2: (4-methoxyphenyl)-boronic acid With potassium carbonate; palladium diacetate in 1,4-dioxane; water T=100°C; Suzuki coupling; 15 h;

1: CH2Cl2 / 3 h / Ambient temperature 2: pyridine, DMAP, Et3N / CH2Cl2 / 16 h / Ambient temperature 3: 96 percent / CF3COOH / CH2Cl2 / 20 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in tetrahydrofuran Heating;

Yield given. Multistep reaction;

Yield given. Multistep reaction;