Cl.[CH3:2][S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C[Al](C)C.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([C:24](=[NH:25])[NH:10][C:9]2[CH:11]=[CH:12][C:6]([S:3]([CH3:2])(=[O:4])=[O:5])=[CH:7][CH:8]=2)=[N:22][CH:23]=1To a suspension of 4-(methylsulfonyl)aniline hydrochloride (10 mmol) in toluene (60 ml) at 0° C., trimethylaluminum (2M solution in toluene, 10 ml, 20 mmol) is added over 10 minutes. The reaction mixture is allowed to warm to room temperature and stirred for 2 hours. A solution of 5-methyl-2-cyanopyridine (20 mmol) in toluene (100 ml) is added over 10 minutes and the mixture is heated to 85°-90° C. After 24 hours, the reaction mixture is cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue is washed with a mixture of methylene chloride and methanol and later with methanol. The combined filtrates are concentrated and the resulting solid is stirred with a mixture of hexane and ethyl acetate (1000 ml) and filtered. The product obtained is used in the next reaction without further purification.
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