[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][N:8]=1.O>CC(N(C)C)=O>[I:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:8][CH:9]=1Pyrrolidine (1.74 ml) was added to 2-chloro-5-iodopyridine (1 g) in dimethylacetamide (5 ml) and the solution heated at 120° C. for 4 h. After cooling, the reaction mixture was poured into water (60 ml) and the solid precipitate collected by filtration. Recrystallisation from ethyl acetate gave the product as off-white needles (0.33 g); the remaining material was adsorbed onto silica and purified by column chromatography eluting with 0 to 3% ethyl acetate in hexane to give a white solid (0.65 g).
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