O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)[C:10]([NH2:12])=O.[C:21]([O-])([O-])=[O:22].[Na+].[Na+]>CN(C=O)C>[CH:21]([C:17]1[N:16]([C:15]2[CH:14]=[CH:13][C:9]([C:10]#[N:12])=[CH:8][C:7]=2[CH3:6])[CH:20]=[CH:19][CH:18]=1)=[O:22]POCl3 (65 g, 427 mmol) was added to DMF (34 mL) at 0° C. for 30 min. After addition, the mixture was stirred at room temperature for 1.5 h, and then cooled to 0° C. A solution of 3-methyl-4-(1H-pyrrol-1-yl)benzamide (6A) (42.7 g, 213.5 mmol) in DMF (150 mL) was added at 0° C. and the resultant mixture was stirred at room temperature for 20 min, and then heated to 80° C. for 1 h. The solution was cooled to room temperature and then sat. Na2CO3 was added at 0° C. until pH=8. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with sat. NaHCO3 and brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=10:1) to afford 4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile as a yellow solid (30.5 g, yield 68%).
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