Morpholine → HCID 70496491, compound

Participants

Reaction Steps

2-(3-bromo-5-fluoro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (3.9 g, 10.0 mmol), morpholine (9.0 mL, 95.0 mmol), copper(I) iodide (1.1 g, 6.0 mmol), N,N-dimethylglycine hydrochloride (1.1 g, 8.0 mmol), and potassium carbonate (4.1 g, 30.0 mmol) in dimethyl sulfoxide (20 mL) was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (200 mL×2), washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 2-(3-fluoro-5-morpholin-4-yl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (3.2 g, 80%) as a white solid: MS (ESI) M+1=399.0.

Provenance & Evidence