Sodium Chloride → 1-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)-thiophen-2-yl]cyclopent-3ene carboxylic acid ethyl ester

Participants

Reaction Steps

To a suspension of petroleum ether washed NaH (1.1 equiv.) in DMF was added 2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine (7) (1.1 equiv.). The reaction mixture was stirred for 15 minutes at ambient temperature and then the product of Step 4, above (5) (1 equiv.), dissolved in DMF, was cannulated into the mixture of the anion in DMF. The reaction mixture was stirred at ambient temperature for 17 hours and was then poured into saturated NaCl solution and extracted 2 times with EtOAc. The combined extracts were dried over MgSO4, filtered and concentrated to dryness. The crude material was chromatographed on silica gel with a gradient elution from 50% EtOAc in hexanes to 60% EtOAc in hexanes to yield the title compound (6).

Provenance & Evidence