Tetrahydrofuran → 1-[6-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)naphthalen-2-yl]cyclopent-3-ene carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Step 3, above (52) (95 mg, 0.24 mmol), in THF/DMPU (1 ml/0.25 ml) at -78° C., was added 1.0M solution of potassium t-butoxide in THF (0.24 ml, 0.24 mmol). The solution was stirred for 15 minutes at -78° C. and cis-1,4-dichlorobut-2-ene (0.025 ml, 0.24 mmol) was added. The reaction mixture was stirred at -78° C. for 10 minutes and a second equivalent of 1.0M potassium t-butoxide solution was added. The reaction mixture was warmed to -50° C. for 15 minutes, the cooling bath was removed and the mixture was stirred at ambient temperature for 15 minutes. The reaction was then heated to 80° C. for 2 hours. The reaction was cooled to ambient temperature, quenched with concentrated acetic acid, diluted with EtOAc and extracted from brine. The combined organics were then dried over MgSO4, filtered and concentrated to dryness. The crude material was then chromatographed on silica gel using 50% EtOAc in hexanes as the eluant to yield the title compound (53) (35 mg).

Provenance & Evidence