1: phenyllithium With zinc(II) chloride in tetrahydrofuran; diethyl ether; cyclohexane T=-78 - 20°C; 0.5 h; 2: 2,4-dibromo-1,3-thiazole With bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran; diethyl ether; cyclohexane T=20°C; Negishi cross-coupling; 16 h; Further stages.;

potassium phosphate; palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in tetrahydrofuran T=60°C; Suzuki coupling; 16 h; Inert atmosphere; regioselective reaction;

1: With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1.16667 h; Inert atmosphere; 2: With water in tetrahydrofuran T=-78 - 20°C; Inert atmosphere;

1.1: N-bromosuccinmide / chloroform / 18 h / 60 °C / Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere View Scheme

1: 4-bromo-2-phenylthiazole With tert.-butyl lithium in diethyl ether; pentane T=-80 - -50°C; Inert atmosphere; 2: With tributyltin chloride in diethyl ether; pentane T=-80°C; Inert atmosphere; 3: thien-2-yl bromide With tetrakis(triphenylphosphine) palladium(0); cesium fluoride in toluene Stille cross-coupling reaction; 24 h; RefluxInert atmosphere;

tetrakis(triphenylphosphine) palladium(0); cesium fluoride in toluene Stille coupling; 16 h; Reflux;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in toluene Suzuki-Miyaura coupling; 16 h; Reflux;

tetrakis(triphenylphosphine) palladium(0); cesium fluoride in toluene Stille coupling; 16 h; Reflux;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in toluene Suzuki-Miyaura coupling; 16 h; Reflux;