[Na].CN(C)[CH:4]=[O:5].Br[C:8]1[CH:23]=[CH:22][C:11]2[NH:12][C:13]3[CH:20]=[CH:19][C:18](Br)=[CH:17][C:14]=3[CH2:15][CH2:16][C:10]=2[CH:9]=1.[K+].[Br-].[CH3:26][OH:27]>[Cu]I.[Cu]>[CH3:26][O:27][C:8]1[CH:23]=[CH:22][C:11]2[NH:12][C:13]3[CH:20]=[CH:19][C:18]([O:5][CH3:4])=[CH:17][C:14]=3[CH2:15][CH2:16][C:10]=2[CH:9]=1A solution of sodium metal (23 g; 1 mol) in anhydrous methanol (250 mL) was treated with dimethylformamide (DMF) (125 mL; dried over molecular sieve 4A), copper(I) iodide (38 g; 199.5 mmol), 2,8-dibromo-10,11-dihydro-5H-dibenz[b,f]azepine (6) (17.9 g; 50.7 mmol) [L. Kricka and A. Ledwitn, J. Chem. Soc. Perkin I, 859 (1973)]and additional DMF (125 mL). The mixture was mechanically stirred and heated (mantle) at reflux (internal temperature was 92° C.) for four hours. After cooling to ca. 35° C. the copper-colored mixture was filtered through Celite (Johns-Manville Corp., Denver, CO, USA) and the cake was washed with ethyl acetate (EtOAc; 500 mL). The combined filtrate and wash were blended into H2O (2 L) and the phases separated. The aqueous layer was extracted twice with EtOAc (500 mL each) then the combined EtOAc layers were washed once with H2O (500 mL), once with brine (saturated aqueous NaCl; 500 mL) and dried over a mixture of MgSO4 (50 g) and Darco G-60 (ICI Americas, Inc., Wilmington, DE, USA; 20 g). The solution was filtered through Celite and concentrated in vacuo to a total volume of 40-50 mL. The concentrate was heated to boiling, diluted with hexane (ca. 60 mL) and allowed to cool to ambient temperature overnight whereupon the title compound (7) (7.04 g) separated as beige plates; the mother liquor was worked for a second crop (1.68 g; total yield 67.6%). A portion of the first crop was sublimed (0.1 torr; 122-4° C. bath) to afford the analytical sample as white plates with mp=123-4° C.: IR (KBr) cm-1 3390, 2946, 1510, 1262, 1221, 1039, 1031, 911, 852, 810; 1H NMR (300.12 MHz) (DMSO-d6) δ2.90 (s, 4H), 3.64 (s, 6H), 6.55-6.65 (m, 4H), 6.83 (d, J=8.5 Hz, 2H), 7.64 (s, lH); 13C NMR (75.47 MHz) (DMSO-d6) ppm 151.9, 137.6, 128.7, 118.7, 115.2, 112.5, 55.2, 34.3; mass spectrum m/e 255, 240 (base), 225, 209, 197, 180, 168.
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