Synthesis of novel annulated hymenialdisine analogues via palladium-catalyzed cross-coupling reactions with aryl boronic acids

Synlett

Volumn , Issue 2, 2010, Pages 211-214

  Mangu, Naveenkumar ^a   Spannenberg, Anke ^a   Beller, Matthias ^a   Tse, Man Kin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Cross coupling; Heterocycles; Hymenialdisine analogues; Palladium; Silica gel

Indexed keywords

BORONIC ACID DERIVATIVE; HYMENIALDISINE; PALLADIUM;

ARTICLE; CATALYSIS; SUZUKI REACTION;

EID: 75649148167     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218573     Document Type: Article

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34. Decomposition of compound 8 was observed on storage (~5 d).
35. General procedure for the Suzuki coupling of 8 with aryl boronic acids 9ak: To a stirring mixture of 8 (600 mg, 1.1 mmol) in toluene (3 mL) and absolute EtOH (3 mL) under an argon atmosphere, Pd(PPh3)4 (12.6 mg, 0.011 mmol), boronic acid (1.2 mmol) and 2 M aq Na2CO3 solution (0.55 mL) were added. The mixture was heated at 70 C overnight (~1216 h), then the solvent was removed under reduced pressure and the mixture was extracted with CH2Cl2 (2 ×20 mL), the combined organic extracts were washed with brine (25 mL), dried over MgSO4 and concentrated under reduced pressure to give the crude product, which was used for the deprotection step without further purification. The above crude product was dissolved in anhydrous CH2Cl2 (50 mL) and activated silica (2.46 g, 0.0400.063 mm) was added. The solvent was removed under reduced pressure and the solid mixture was heated under argon at 100 C for 1 h. Purification by column chromatography (silica gel 70230 mesh, hexaneEtOAc, 6:4) yielded pure compounds 9ak.
36. X-ray crystal data for 9d: Empirical formula: C19H16N2O2; Mr = 304.34; monoclinic; space group: P21/c; cell dimensions: a = 9.3756 (3), b = 6.5948 (2), c = 25.3990 (8) , b = 100.003 (2); V = 1546.55 (8) 3; Z = 4; rcalcd = 1.307 gcm3; 22763 reflections measured, 3292 independent reflections, of which 2312 were observed [I 2s(I)], final R indices [I 2s(I)]: R1 = 0.0306, wR2 = 0.0686, R indices (all data): R1 = 0.0486, wR2 = 0.0715, 217 refined parameters. Data were collected on a STOE IPDS II diffractometer using graphite-monochromated MoKa radiation. The structure was solved by direct methods (SHELXS-97)19 and refined by full-matrix least-squares techniques on F2 (SHELXL- 97).19 XP (Bruker AXS) was used for graphical representation. CCDC 748111 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.