C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:15][C:16]1[C:24]2[C:23]([NH2:25])=[N:22][CH:21]=[N:20][C:19]=2[O:18][CH:17]=1.N[C:27]1[CH:31]=[C:30]([CH3:32])N[C:28]=1[C:33]([O:35][CH2:36]C)=O>[Cu](I)I.CN(C=O)C>[CH3:36][O:35][C:33]1[CH:28]=[CH:27][C:31]([NH:25][C:23]2[C:24]3[C:16]([CH3:15])=[CH:17][O:18][C:19]=3[N:20]=[CH:21][N:22]=2)=[CH:30][CH:32]=1
A 50 mL round bottom flask with a stir bar was charged with copper iodide (66.5 mg, 0.35 mmol), anhydrous potassium carbonate (480 mg, 3.5 mmol), L-proline (80 mg, 0.7 mmol), 5 (150 mg, 1 mmol) and 6 (350 mg, 3.5 mmol). The flask was connected to vacuum for 3 min followed by the addition of anhydrous DMF (15 mL) using syringe. The flask was purged with argon for 5 min and then heated in an oil bath maintained at 110° C. On heating the suspension became bluish grey which lasted for about 2 h. The reaction was stirred for additional 22 h at 110° C. at the end of which the mixture was allowed to cool to room temperature. Ethyl acetate (25 mL) was added and the mixture was poured into water (100 mL). The product was extracted with ethyl acetate (100 mL×2) The combined organic extracts were washed with brine (100 mL) and dried (anhydrous sodium sulfate) and concentrated under reduced pressure. Silica gel (500 mg) was added and solvent evaporated to obtain a plug. Purification by column chromatography using hexanes and ethyl acetate (10:1 to 2:1) afforded 7 (140 mg, 56%) as light brown solid. TLC Rf0.77 (CHCl3:MeOH, 10:1); mp 99-101.6° C.; 1HNMR (400 MHz) (DMSO-d6). δ 2.383-2.386 (d, 3H, CH3, J=1.2 Hz); 3.747 (s, 3H, OCH3), 6.919-6.941 (d, 2H, C6H4, J=8.8 Hz), 7.466-7.488 (d, 2H, C6H4, J=8.8 Hz), 7.65-7.653 (d, 1H, C6-CH, J=1.2 Hz), 8.234 (s, 1H, C2-CH), 8.381 (s, 1H, 4-NH, exch). Anal. Calcd for C14H13N3O2: C, 65.87; H, 5.13; N, 16.46; Found: C, 65.94; H, 5.13; N, 16.42.
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