Toluene → N-((S)-6-Pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

A mixture of N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (1.00 g), toluene (10 ml) and Pd(PPh3)4 (2.69 g) was admixed with 3-pyridylboronic acid (0.28 g), ethanol (3 ml) and cesium carbonate solution (1.2 ml; 2 M in water). The mixture was boiled at reflux for 7 hours. The cooled reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product was thus obtained with the molecular weight of 428.54 (C27H28N2O3); MS (ESI): 429 (M+H+).

1. temperatureat reflux for 7 hours
2. customThe cooled reaction mixture
3. washwashed with water
4. washThe organic phase was washed with sodium chloride solution
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by chromatography on silica gel
8. customThe product was thus obtained with the molecular weight of 428.54 (C27H28N2O3)

ORD-Eintrag

ord-b99976bca4f34394aedcc9c9c4d5f2b1

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08609731B2