Pyridine → 3-Ethynyl-5-(pyrrolidin-1-ylmethyl)pyridine

Participants

Reaction Steps

4-methyl-3-{[5-(pyrrolidin-1-ylmethyl)pyridin-3-yl]ethyl}benzoic acid can be prepared in a manner similar to that described above for the Sonogashira reaction. 3-Ethynyl-5-<pyrrolidin-1-ylmethyl)pyridine and 3-iodo-4-methylbenzoic acid are used as coupling partners. Alternatively, the solvent (DMF) can be replaced by ethyl acetate and the base (Hunig base) can be replaced by triethylamine. The product can be isolated by filtration of the crude reaction mixture. The filter cake is washed sequentially with a solvent such as ethyl acetate and then water, then dried in a vacuum oven. Further purification can be achieved by slurrying the solids in water adjusted to pH 3 with the addition of concentrated HCl. After filtration and water wash, the product can be dried in a vacuum oven.

Provenance & Evidence