Compound 21
4-(1-methyl-1H-imidazol-5-yl)pyridine
From: Fragment-based discovery of a chemical probe for the PWWP1 domain of NSD3
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a mixture of 4-bromo-pyridine (19) (1.00 g; 6.33 mmol) and 1-methyl-1H-imidazole (20) (0.76 ml; 9.49 mmol) in dimethylacetamide (20 ml) was added potassium acetate (1.24 g; 12.66 mmol) under argon atmosphere. Palladium(II) acetate (0.14 g; 0.63 mmol) was added and the mixture heated to 150°C for 16 h. After cooling to room temperature, the reaction mixture was quenched with ice water, extracted with EtOAc and the organic layer dried over Na2SO4, filtered and evaporated. The product was purified by column chromatography on silica gel to obtain 4-(3-methyl-3H-imidazol-4-yl)-pyridine (21) (1.0 g; 6.28 mmol, 99%).
