2-Methoxypyrimidine-5-boronic acid → (3-amino-2,6-difluoro-phenyl)-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanone

温度

160 °C

In a microwave vial, (3-amino-2,6-difluoro-phenyl)-(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (19, 1.36 g, 3.41 mmol), 2-methoxy-pyrimidine-5-boronic acid (20, 1.05 g, 6.81 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.25 g, 0.34 mmol) were mixed in 22 mL of 1.00 M potassium carbonate in water and 18 mL of acetonitrile. The resulting mixture was heated at 160° C. in the microwave for 15 minutes. The resulting mixture was filtered through a thin layer of celite, and the celite bed was washed with a mixture of water and ethyl acetate. The two layers of the filtrate were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and the filtrate concentrated under vacuum. The residue was purified by flash silica gel chromatography eluting with ethyl acetate and dichloromethane to provide the desired compound (21, 0.567 g). MS (ESI) [M+H+]+=382.1.

1. filtrationThe resulting mixture was filtered through a thin layer of celite, and the celite bed
2. washwas washed with a mixture of water and ethyl acetate
3. customThe two layers of the filtrate were separated
4. extractionthe aqueous layer was extracted with ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationthe filtrate concentrated under vacuum
9. customThe residue was purified by flash silica gel chromatography
10. washeluting with ethyl acetate and dichloromethane

ORDレコード

ord-0fe67580fcf141079f561e1207acb3e2

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08198273B2