5-[(3-Nitropyrid-2-yl) amino] indoles: Novel serotonin agonists with selectivity for the 5-HT1D receptor. Variation of the C3 substituent on the indole template leads to …

…, LA Lebel, ME Newman, RJ Post, K Ryan…

Index: Macor; Blank; Fox; Lebel; Newman; Post; Ryan; Schmidt; Schulz; Koe Journal of Medicinal Chemistry, 1994 , vol. 37, # 16 p. 2509 - 2512

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Citation Number: 32

Abstract

15 (a) 2-Chloro-3-nitropyridine, triethylamine, dioxane, A (67%);(b) benzyl bromide, triethylamine, acetonitrile, A (88%);(c)(1) EtMgBr (2 equiv), indole (2 equiv), benzene, 0" C;(2) CBZ-proline acid chloride, benzene, 0-25" C (44%);(d) lithium aluminum hydrideflithium borohydride, THF, A (89%);(e) palladium hydroxide on carbon, Hz, ethanol (99%);(f) 2-chloro-3-nitropyridine, triethylamine, acetonitrile, A (81%);(g) lithium ...