Chloride → HCID 68965552, compound

Participants

Reaction Steps

Make the free base of 2-chloroethylpyrrolidine by adding the hydrochloride salt (84 mg, 0.49 mmol) to a separatory funnel containing 1 N NaOH (75 mL) and CH2Cl2 (75 mL). Wash the organic layer with brine then dry over Na2SO4 and concentrate. In a separate microwave vessel, mix 2-(4-cyclopropoxy-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (100 mg, 0.24 mmol) in DMF (1 mL). Warm the mixture slightly with a heat gun until the phenol is in solution. Add powdered K2CO3 (68 mg, 0.49 mmol). Stir 5-10 min at RT and then add the chloride mentioned above as a solution in DMF (500 μL). Cap the vessel and heat under microwave irradiation to 110° C. for 2 h. Load the reaction directly onto a silica gel plug and purify via silica gel chromatography using a 0-10% gradient of (2 N NH3 in MeOH)/CHCl3. Dissolve the freebase of the product in CH2Cl2 (10 mL) and add 1.0 M HCl in Et2O (266 μL). Concentrate to give 48 mg (36%) of the desired product. MS/ES m/z 505.3 [M+H]+.

Provenance & Evidence