[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]2[O:21][C:22]([CH3:24])=[CH:23][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:31]([O:37][CH2:38][CH3:39])(=[O:36])[C:32]#[C:33][CH2:34][CH3:35]>CN(C)C=O.O>[CH2:34]([C:33]1[C:32]([C:31]([O:37][CH2:38][CH3:39])=[O:36])=[C:16]2[C:17]3[CH:23]=[C:22]([CH3:24])[O:21][C:18]=3[CH:19]=[CH:20][N:15]2[N:14]=1)[CH3:35]
A mixture of 5-amino-2-methylfuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (1.44 g, 4.33 mmol), potassium carbonate (838 mg, 6.06 mmol) and ethyl 2-pentynoate (628 μL, 4.76 mmol) in dimethylformamide (20 mL) was stirred at room temperature for 14 hr. The reaction solution was diluted with water, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (451 mg, yield 38%).
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