Br[C:2](C)([C:6]1[C:7](=[C:11](C)[CH:12]=[CH:13][CH:14]=1)[C:8]([O-])=[O:9])C([O-])=O.[C:17]([C:19]1[C:20]([OH:26])=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=1)#[N:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:25][C:22]1[N:21]=[C:20]2[C:19]([C:17]3[NH:18][C:8](=[O:9])[C:7]4[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=4[C:2]=3[O:26]2)=[CH:24][CH:23]=1To a solution of α-bromodimethylhomophthalate (2.00 g, 6.97 mmol) in DMF (15 mL) was added 3-cyano-2-hydroxy-6-methylpyridine (1.03 g, 1.1 eq) and potassium carbonate (4.82 g, 5 eq). The resulting mixture was allowed to stir at 100° C. for 4 h under inert atmosphere. The reaction was cooled to room temperature and concentrated in vacuo. The resulting solid residue was diluted with 1 N aqueous HCl (60 mL) and stirred for 30 min. The resulting suspension was filtered and the solids were washed with water. The aqueous filtrate was extracted with EtOAc (2×50 mL). The collected solids were added to the combined EtOAc extracts, and the resulting solution was dried over sodium sulfate, filtered and concentrated in vacuo to afford a crude residue. The crude residue was recrystallized from toluene at −20° C. over 18 h, vacuum filtered and dried to provide compound 26a as a yellow solid. Yield=500 mg (29%).
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