synthesis and catalytic functionalization of biologically active indoles

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3 Publications 97 3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-5-pyrrolidin-1-yl-1H-indole (5i) Yield: 73%. Mp: 150-155 °C. 1 H NMR (300.13, CDCl3): � = 7.23 (d, 1H, J = 8.6 Hz); 6.70-6.50 (m, 2H); 3.55 (s, 3H); 3.31 (t, 4H, J = 6.2 Hz); 2.27 (s, 3H); 2.03 (t, 4H, J = 6.2 Hz); 1.09 (s, 9H); 0.17 (s, 6H)ppm. 13 C NMR (CDCl3, 75.5 MHz): 144.8 (q); 130.3 (q); 130.0 (q); 123.3 (q); 121.9 (q); 113.8; 109.1; 104.5; 48.9 (CH2)2; 29.8; 26.1; 25.5 (CH2)2; 18.4 (q); 9.5; -3.9 ppm. MS (EI, 70 eV) m/z (rel. intensity): 344 (M + , 100), 287 (8), 229 (5), 73 (9). HRMS Calcd. for C20H32N2OSi: 344.22784. Found: 344.227392. FTIR (KBr): 3433, 3078, 2954, 2927, 2893, 2856, 1806, 1626, 1498, 1480, 1376, 1356, 1314, 1302, 1286, 1250, 1175, 906, 897, 838, 777 cm -1 OTBDMS N CH3 N CH3 . [3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-1H-indol-5-yl]-hexyl-amine (5j) Yield: 95%. Mp.: 83-90°C. 1 H NMR (300.13, CDCl3): � = 7.01 (d, 1H, J = 8.4 Hz); 6.67 (d, 1H, J = 2.2 Hz); 6.54 (dd, 1H, J = 2.2 Hz, J = 8.4 Hz); 3.53 (s, 3H); 3.13 (t, 2H, J = 7.1 Hz); 2.25 (s, 3H); 1.70-1.58 (m, 2H); 1.50-1.20 (m, 6H); 1.1 (s, 9H); 0.92 (t, 3H, J = 6.7 Hz); 0.17 (s, 6H) ppm. 13 C NMR (CDCl3, 75.5 MHz): � = 141.6 (q); 129.9 (q); 128.9 (q); 123.0 (q); 122.4 (q); 110.9; 109.2; 99.8; 46.0 (CH2); 32.0 (CH2); 29.9 (CH2); 29.7; 27.2 (CH2); 26.1; 22.9 (CH2); 18.4 (q); 14.3; 9.4; -3.9 ppm. MS (EI, 70 eV) m/z (rel. intensity): 375 (M +1 , 28), 374 (M + , 100), 304 (13), 303 (57), 245 (3), 244 (8), 173 (18), 142 (7), 84 (10). HRMS Calcd. for C22H38N2OSi: 374.27479. Found: 374.274037. FTIR (Nujol): 3395, 2927, 2856, 1624, 1568, 1463, 1378, 1282, 1246, 1168, 1069, 1006, 939, 895, 841, 778, 728 cm -1 H OTBDMS N CH3 N CH3 .
3 Publications 98 3.4 Palladium-Catalyzed C-O and C-C Coupling Reactions of Electron-Rich Indoles Nicolle Schwarz, Anahit Pews-Davtyan, Karolin Alex, Annegret Tillack, Matthias Beller, Synthesis 2007, 23, 3722-3730. Contributions: In this paper I contributed to a significant amount of the argumentation and the synthetic work. I performed all catalytic investigation. My contribution as co-author of this paper is approximately 80%.
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Leibniz-Institut für Katalyse e. V
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Für meine Eltern Siegfried und Ker
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List of Abbreviations Ac Acetyl aq
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Preface The search for drugs is an
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