synthesis and catalytic functionalization of biologically active indoles

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2898 N. Schwarz et al. / Tetrahedron Letters 48 (2007) 2897–2900 Table 1. Reaction of 3-tert-butyldimethylsilyloxy-5-bromo-indole with benzylamine in the presence of different ligands and bases a Br OTBDMS H2N HN CH3 + 5 N CH3 5a OTBDMS CH3 N CH3 Entry Ligand Base Yield b (%) 1 N P LiHMDS 6 c 2 K3PO4 85 5 3 4 Cs2CO3 NaO 70 t Bu 40 5 Without 0 6 7 8 9 10 11 N N Si P P 7 8 PCy3 NMe2 P P N 9 10 11 12 P LiHMDS
Table 2. Reaction of different amines with the silyl-protected 3-oxy-5-bromo-2-methylindole a Br 5 OTBDMS CH3 N CH3 + R HN 1 R2 Pd(OAc) 2 ligand 6 R1 N R2 OTBDMS CH3 N CH3 5a-j Entry Amine Product Yield b (%) 1 2 NH 2 3 NH 2 4 5 6 F 7 HN 8 HN O 9 NH HN HN OTBDMS CH3 N CH3 OTBDMS NH2 N CH3 CH3 HN OTBDMS CH3 N CH3 NH2 N CH3 CH3 NH 2 10 NH 2 N. Schwarz et al. / Tetrahedron Letters 48 (2007) 2897–2900 2899 F H N H N OTBDMS OTBDMS CH3 N CH3 CH3 HN N N CH3 O N N N N N OTBDMS CH3 N CH3 OTBDMS CH3 N CH3 OTBDMS CH3 N CH3 H N OTBDMS OTBDMS CH3 N CH3 5a 85 5b 40 5c 85 5d 60 5e 91 5f 50 5g 8 75 5h 55 5i 73 5j 91 a Reaction conditions: 3-tert-butyldimethylsilyloxy-5-bromo-2-methylindole (0.56 mmol), amine (0.67 mmol), solvent: toluene (3 mL), 1 mol % Pd(OAc) 2, 2 mol % ligand 6, 1 M solution of lithium-bis(trimethylsilyl)amide in toluene (0.73 mmol), 24 h, 100 °C. b Isolated yield based on 3-tert-butyldimethylsilyloxy-5-bromo-2-methylindole.
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Leibniz-Institut für Katalyse e. V
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Für meine Eltern Siegfried und Ker
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Mein besonderer Dank gilt Dr. Anneg
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Table of Contents Preface .........
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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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1 Palladium-catalyzed Coupling Reac
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Page 151 and 152: DOI: 10.1002/cssc.200700160 General
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Zn-Catalyzed Hydroamination of Term
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Zn-Catalyzed Hydroamination of Term
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3 Publications 146 3.10 Zn-Catalyze
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Over the past years, we investigate
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3 Publications 150 3.11 First Synth
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4608 K. Alex et al. / Tetrahedron L
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Publikationen 1 Titanium-Catalyzed
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