2-Amino-4-methylpyridine → Ethyl 1-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (434 mg, 0.70 mmol) and palladium acetate (117 mg, 0.52 mmol) was dissolve in toluene (15 ml), and after 2-amino-4-picoline (395 mg, 3.65 mmol) and a toluene (15 ml) solution of ethyl 1-[5-(6-bromopyridin-2-yl)thiazol-2-yl]piperidine-4-carboxylate obtained by Step 2 (1.38 g, 3.48 mmol) were sequentially added, cesium carbonate (1.70 g, 5.22 mmol) was added and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution and extracted with ethyl acetate and washed with a saturated brine. The organic layer was dried over anhydrous sodium sulfate and the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1 to 1:10) and the title compound (817 mg, 55%) was obtained.

Provenance & Evidence