2-Amino-4-methylpyridine → 3-(1-{5-[6(4-Methyl-pyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acid methyl ester

Temperature

100 °C

rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (91 mg, 0.15 mmol) and palladium acetate (25 mg, 0.11 mmol) were suspended in toluene (7 ml), and after 2-amino-4-picoline (79 mg, 0.73 mmol) and 3-{1-[5-(6-bromopyridin-2-yl)-thiazol-2-yl]piperidin-4-yl}propionic acid methyl ester (300 mg, 0.73 mmol) obtained in Step 2 were sequentially added, cesium carbonate (357 mg, 1.1 mmol) was added, and the mixture was stirred overnight at 100° C. Water was added to the reaction solution and the solution was 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 chromatography on silica gel (n-hexane:ethyl acetate=1:1 to 1:10) and the title compound (250 mg, 55%) was obtained.

1. extractionthe solution was extracted with ethyl acetate
2. washwashed with a saturated brine
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. customthe residue obtained by vacuum concentration
5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=1:1 to 1:10)

ORD record

ord-55a059425f444a97aa47d6b13da1752b

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803801B2