tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 1 h;

1: With sec.-butyllithium in tetrahydrofuran; cyclohexane T=-78°C; 0.5 h; 2: With carbon tetrabromide in tetrahydrofuran; cyclohexane T=-78°C; 0.416667 h; Further stages.;

1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine With sec.-butyllithium in tetrahydrofuran; cyclohexane T=78°C; 0.5 h; Inert atmosphere; 2: carbon tetrabromide in tetrahydrofuran; cyclohexane 2 h;

1.1: sodium hydride / tetrahydrofuran; hexane / 0.25 h / 0 °C 1.2: 93.5 percent / tetrahydrofuran; hexane / 18 h / 80 °C 2.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 2.2: 80 percent / carbon tetrabromide / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C View Scheme

1.1: sodium hydride / tetrahydrofuran; hexane / 0.25 h / 0 °C 1.2: 93.5 percent / tetrahydrofuran; hexane / 18 h / 80 °C 2.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 2.2: 80 percent / carbon tetrabromide / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / hexane; ethylene glycol dimethyl ether / 3 h / 20 °C 2.1: methanesulfonyl chloride / N,N-dimethyl-formamide / 2 h / 70 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / |Inert atmosphere 3.2: 50 °C / |Inert atmosphere 4.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / 78 °C / |Inert atmosphere 4.2: 2 h View Scheme

1.1: methanesulfonyl chloride / N,N-dimethyl-formamide / 2 h / 70 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / |Inert atmosphere 2.2: 50 °C / |Inert atmosphere 3.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / 78 °C / |Inert atmosphere 3.2: 2 h View Scheme