Dichloromethane → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-4-yl)benzo[d]thiazol-6-yl)acetate

Temperatur

100 °C

To a solution of 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.284 mmol) in dioxane (3 mL) was added bis(pinacolato)diboron (87 mg, 0.341 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (23 mg, 0.028 mmol), potassium acetate (84 mg, 0.852 mmol). The mixture was degassed and heated at 100° C. for 2 h. The mixture was cooled, and then added (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (100 mg, 0.189 mmol), tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.019 mmol), K2CO3 (131 mg, 0.948 mmol) and water (1 mL, degassed). The reaction mixture was heated at 110° C. for 1 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4 and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C35H33ClN4O3S: 625.2 (M+H+); Found: 625.3 (M+H+).

1. customThe mixture was degassed
2. temperatureThe mixture was cooled
3. temperatureThe reaction mixture was heated at 110° C. for 1 h
4. temperaturecooled
5. custompartitioned between ethyl acetate and brine
6. customThe organic layer was separated
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customto give crude which
10. customwas purified by chromatographic column

ORD-Eintrag

ord-78ea7fcce26f444c887371ac584749c7

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08987250B2