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Synlett 2012; 23(18): 2603-2608
DOI: 10.1055/s-0032-1317329
DOI: 10.1055/s-0032-1317329
letter
Transition-Metal-Catalyzed Arylation of 1-Deazapurines via C–H Bond Activation
Further Information
Publication History
Received: 02 August 2012
Accepted after revision: 06 September 2012
Publication Date:
01 October 2012 (online)
Abstract
Transition-metal-catalyzed arylation of imidazo[4,5-b]pyridines (known as 1-deazapurines) is reported. 1-Deazapurines were synthesized from 5-aminoimidazoles, generated in situ by the reaction of methyl N-(cyanomethyl)formimidate with primary amines.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 28 3-Phenethyl-2-phenyl-5-(thiophen-2-yl)-7-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (6i): Bright-yellow solid; mp 137–139 °C; 1H NMR (300.13 MHz, CDCl3): δ = 3.14 (t, J = 6.99, 2 H, CH2), 4.57 (t, J = 7.55, 2 H, CH2), 6.99 (d, J = 8.12 Hz, 2 H, ArH), 7.12–7.16 (m, 2 H, ArH), 7.28–7.44 (m, 5 H, ArH), 7.51–7.59 (m, 2 H, ArH), 7.63 (d, J = 7.18 Hz, 2 H, ArH), 7.76 (s, 1 H, ArH); 13C NMR (62.89 MHz, CDCl3): δ = 35.6 (CH2), 45.6 (CH2), 110.3 (q, 3 J C–F = 4.12 Hz, CH), 122.8 (q, 1 J C–F = 274.00 Hz, CF3), 124.2 (CH), 125.8 (2CH), 126.0 (CH), 126.9 (CH), 127.9 (CH), 128.3 (q, 2 J C–F = 33.88 Hz, C), 128.7 (CH), 128.8 (3CH), 129.0 (CH), 129.3 (CH), 129.5 (C), 130.4 (CH), 134.2 (C), 137.4 (C), 143.4 (C), 146.6 (C), 149.8 (C), 156.5 (C); 19F NMR (282.40 MHz, CDCl3): δ = –61.99 (ArCF3); IR (ATR): 3025 (w), 2960 (s), 2927 (m), 2868 (w), 1907 (w), 1732 (w), 1600 (m), 1544 (m), 1496 (m), 1467 (w), 1453 (w), 1443 (w), 1418 (w), 1384 (s), 1367 (w), 1339 (w), 1329 (w), 1309 (w), 1271 (m), 1250 (m), 1228 (w), 1155 (w), 1125 (s), 1099 (w), 1073 (w), 1049 (w), 1029 (w), 1020 (w), 1004 (w), 959 (w), 942 (w), 929 (w), 898 (w), 868 (m), 846 (w), 833 (w), 809 (s), 779 (w), 755 (m), 739 (w), 696 (w), 684 (m), 666 (w), 618 (w), 609 (w), 586 (w), 558 (m), 532 (w) cm–1; GC-MS (EI, 70 eV): m/z (%) = 449 (26) [M]+, 358 (2), 345 (100), 324 (1), 242 (1), 208 (2), 186 (1), 146 (1), 105 (1), 91 (1), 77 (2); HRMS (ESI): m/z [M + H]+ calcd for C25H19F3N3S: 450.12463; found: 450.12452
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