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Synlett 2014; 25(14): 2064-2066
DOI: 10.1055/s-0034-1378526
DOI: 10.1055/s-0034-1378526
letter
Regioselective Cross-Dehydrogenative Coupling of Indole-2-carboxylic Acids and Pyridine-N-oxides Followed by Protodecarboxylation
Further Information
Publication History
Received: 16 May 2014
Accepted after revision: 20 June 2014
Publication Date:
28 July 2014 (online)
Abstract
Regioselective coupling at the ortho position rather than at the ipso position of heteroaryl carboxylic acids with pyridine N-oxide has been reported.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
-
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- 14 General Procedure for the Preparation of Substituted Pyridine-N-oxide (3) A mixture of substituted pyridine N-oxide 1 (1 equiv), heteroaryl carboxylic acid 2 (2 equiv), Pd(OAc)2 (10 mol%), pyridine (3 equiv), and Ag2O (2.5 equiv) in DMF–MeCN (1:2, 6 mL) was stirred at 110 °C for 12 h. The reaction mixture was filtered through a Celite pad and the pad washed with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified on either a CombiFlash Rf or a Grace Instruments chromatography system on Teledyne Isco RediSep Rf columns (normal phase, 12 g) with 2–4% MeOH in CH2Cl2 as eluent to obtain 3. Representative Analytical Data of Compound 3a 1H NMR (400 MHz, CDCl3): δ = 7.27–7.30 (m, 2 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.52 (t, J = 8.4 Hz, 2 H), 7.61 (t, J = 8.4 Hz, 1 H), 7.73 (dd, J = 8.0 1.4 Hz, 1 H), 8.17 (dd, J = 8.0, 1.4 Hz, 1 H), 8.30 (d, J = 8.4 Hz, 2 H), 8.44 (d, J = 6.4 Hz, 1 H), 8.52 (dd, J = 4.8, 1.4 Hz, 1 H), 8.85 (s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 110.7, 119.3, 120.9, 123.9, 125.4, 126.1, 128.4, 128.9, 129.1, 130.4, 134.4, 139.9, 140.7, 143.0, 145.4, 146.8. LC–MS [M + 1]: 352. Anal. Calcd for: C18H13N3O3S: C, 61.53; H, 3.73; N, 11.96. Found: C, 61.50; H, 3.77; N, 11.90.