Potassium Carbonate → HCID 11394127, compound

Participants

Reaction Steps

A solution of 9-BBN (0.5 N in THF, 100 mL) was added 4-methylenepiperidine-1-carboxylic acid tert-butyl ester (1.23 g, 1.5 mmol) the reaction mixture was stirred at reflux for 1 h. The reaction mixture was cooled to RT and added via a syringe to a solution of 2,5-dibromopyridine (11.3 g, 47.5 mmol) and Pd(dppf)Cl2 dichloromethane (1.23 g, 1.5 mmol) dissolved in DMF (100 mL) and water (9.9 mL) and K2CO3 (8.29 g). This mixture was heated at 60° C. for 3 hours. The DMF was the removed in vacuo. Addition of Ethylactetate/heptane afforded only some crystallisation. Therefore was the crude mixture evaporated once more to an oil. Further purification on a CombiFlash with Ethyl actetate/heptane (9:1) as eluent afforded 4-(5-bromopyridin-2-ylmethyl)piperidine-1-carboxylic acid tert-butyl ester as a brown oil. Yield: 8 g, (45%).

Provenance & Evidence