[H-].[Na+].[NH:3]1[CH:8]=[CH:7][CH:6]=C[C:4]1=[O:9].Br[CH2:11][C:12]#[C:13][CH2:14][CH3:15].[Cl-:16].[NH4+:17].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CN(C=O)C>[Cl:16][C:20]1[CH:19]=[CH:18][C:23]([C:7]2[CH:8]=[N:3][C:4](=[O:9])[N:17]([CH2:11][C:12]#[C:13][CH2:14][CH3:15])[CH:6]=2)=[CH:22][CH:21]=1To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid.
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