Methyl iodide → HCID 66673531, compound

Participants

Reaction Steps

Dissolve ((R)-1-{5-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-pyridin-2-yl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (0.367 g, 0.70 mmol) in DMF (10 mL). Treat the mixture with 60% NaH (33.7 mg, 0.84 mmol). Stir the resulting suspension at room temperature for 1 h. Add iodomethane (66 μL, 1.05 mmol) and stir at room temperature for 3 h. Quench the mixture with water (35 mL) and extract with EtOAc (3×40 mL). Wash the combined organic layers with water (3×30 mL), dry with Na2SO4, filter, and concentrate. Dissolve the resulting crude material in CH2Cl2 (5 mL), treat with TFA (3 mL) and stir at room temperature for 1 h. Remove the excess reagent in vacuo. Dilute the residue with CHCl3 (40 mL) and wash with 2.0 M NaOH (30 mL). Treat the cloudy organic layer with CH3OH (1.0 mL), dry with Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 10% CH3OH (with 2M NH3)/CHCl3 to give 0.222 g (72%) of 2-(4-chloro-phenyl)-6-[6-((R)-3-methylamino-pyrrolidin-1-yl)-pyridin-3-yl]-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one.

Provenance & Evidence