[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4]1.O.[C:11]([C:13]1[CH:18]=[C:17](Cl)[N:16]=[C:15]([Cl:20])[CH:14]=1)#[N:12]>CN1CCCC1=O>[Cl:20][C:15]1[CH:14]=[C:13]([C:11]#[N:12])[CH:18]=[C:17]([O:9][CH2:8][C:5]2[CH:6]=[CH:7][S:3][CH:4]=2)[N:16]=1Sodium hydride (0.24 g (ca.60% in mineral oil), 0.006×1.0 mol) was suspended in 20 ml of N-methyl-2-pyrrolidinone, and 3-thiophenemethanol (0.69 g, 0.006×1.0 mol) was added thereto and the resultant solution was stirred for about 30 minutes at room temperature. The resultant mixture was cooled to 4° C. with iced water, then 4-cyano-2,6-dichloropyridine (1.04 g, 0.006 mol) was added thereto and stirred for about 1.5 hour while cooling with iced water.
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