[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:4]([C:12]2[NH:11][CH:15]=[CH:14][CH:13]=2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1A solution of 2-chloronicotinoyl chloride (1 eq.) in dichloromethane (10 mL) was added slowly to a mixture of pyrrole (1.5 eq.) (Aldrich, Milwaukee, Wis.) and aluminum chloride (3.5 g, 1 eq.) in dichloromethane (8 mL) at 0° C. The mixture was stirred at 0° C. for 10 mins and at room temperature for 30 mins. The reaction was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 2.27 g of (2-chloro-pyridin-3-yl)-(1H-pyrrol-2-yl)-methanone.
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