Cesium carbonate → Methyl 2-[(2-methoxyethoxy)methoxy]-3-(5-methoxypyridin-2-ylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-2-((2-methoxyethoxy)methoxy)benzoic acid methyl ester 1.25 g (4.9 mmol) of step 2 in 1,4-dioxane 10 mL were added 2-chloro-5-methoxypyridine 0.70 g (4.9 mmol), Pd(OAc)2 0.11 g (0.49 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 0.31 g (0.49 mmol) and Cs2CO3 3.85 g (9.8 mmol), followed by stirring at 90° C. for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, diluted with ethylacetate, and washed with a saturated sodium bicarbonate solution and a saturated NaCl solution. After drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2) afforded 1.2 g of the title compound (yield 68%).

Provenance & Evidence