tetramethyl-ammonium iodide; boron trichloride T=-78 - 0°C; 2 h; Inert atmosphere;

hydrogenchloride; methanol in dichloromethane T=0°C; 48 h;

1H-imidazole in ethanol 0.75 h; Heating / reflux;

pyridine hydrochloride T=220°C; Inert atmosphere;

1: 1.2 g / H2, N-methylpyrrolidinone / 5percent Pd/C / 54 h 2: 0.42 g / benzoyl chloride, DMF / 0.17 h / 100 - 110 °C 3: 0.47 g / imidazole / ethanol / 0.75 h / Heating View Scheme

1: trifluorormethanesulfonic acid / dichloromethane / 1.5 h / 80 °C 2: sodium hydroxide / water / 4 h / 0 °C 3: copper(ll) bromide / ethyl acetate; chloroform; methanol / 4 h / 70 °C 4: 1H-imidazole / dichloromethane / 1.25 h / 20 °C 5: sodium tetrahydroborate / ethanol / 1 h / 20 °C 6: toluene-4-sulfonic acid / toluene / 0.33 h / 80 °C / |Microwave irradiation 7: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 80 °C 8: hydrogen fluoride; pyridine / tetrahydrofuran / 5 h / 20 °C View Scheme

1: copper(ll) bromide / ethyl acetate; chloroform; methanol / 4 h / 70 °C 2: 1H-imidazole / dichloromethane / 1.25 h / 20 °C 3: sodium tetrahydroborate / ethanol / 1 h / 20 °C 4: toluene-4-sulfonic acid / toluene / 0.33 h / 80 °C / |Microwave irradiation 5: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 80 °C 6: hydrogen fluoride; pyridine / tetrahydrofuran / 5 h / 20 °C View Scheme

1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 80 °C 3: hydrogen fluoride; pyridine / tetrahydrofuran / 5 h / 20 °C View Scheme

1: 1H-imidazole / dichloromethane / 1.25 h / 20 °C 2: sodium tetrahydroborate / ethanol / 1 h / 20 °C 3: toluene-4-sulfonic acid / toluene / 0.33 h / 80 °C / |Microwave irradiation 4: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 80 °C 5: hydrogen fluoride; pyridine / tetrahydrofuran / 5 h / 20 °C View Scheme

1: sodium hydroxide / water / 4 h / 0 °C 2: copper(ll) bromide / ethyl acetate; chloroform; methanol / 4 h / 70 °C 3: 1H-imidazole / dichloromethane / 1.25 h / 20 °C 4: sodium tetrahydroborate / ethanol / 1 h / 20 °C 5: toluene-4-sulfonic acid / toluene / 0.33 h / 80 °C / |Microwave irradiation 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 80 °C 7: hydrogen fluoride; pyridine / tetrahydrofuran / 5 h / 20 °C View Scheme