Reaktion #597466

Reaktionsgleichung

K2CO3

(S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

6-bromo-1-methyl-1H-pyrazolo[4,3-b]pyridine

bis(pinacolato)diboron

dichloromethane

potassium acetate

→

desired product

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridine-6-yl)benzo[d]thiazol-6-yl)ethyl pivalate

Lösungsmittel

water

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   TemperaturThe mixture was cooled
3. 3
   TemperaturThe reaction mixture was heated at 90° C. for 1 h
4. 4
   Temperaturcooled
5. 5
   Sonstigepartitioned between ethyl acetate and brine
6. 6
   SonstigeThe organic layer was separated
7. 7
   Trocknendried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto give crude product which
11. 11
    Sonstigewas purified by chromatographic column

Vorschrift

To a solution of 6-bromo-1-methyl-1H-pyrazolo[4,3-b]pyridine (20 mg, 0.094 mmol) in dioxane (2 mL) was added bis(pinacolato)diboron (29 mg, 0.113 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (8 mg, 0.0094 mmol), potassium acetate (19 mg, 0.189 mmol). The mixture was degassed and heated at 100° C. for 2 h. The mixture was cooled, and then added (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (25 mg, 0.046 mmol), tetrakis(triphenylphosphine)palladium(0) (6 mg, 0.005 mmol), K2CO3 (33 mg, 0.23 mmol) and water (0.3 mL, degassed). The reaction mixture was heated at 90° C. for 1 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give crude product which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C32H35ClN4O3S: 591.22 (M+H+); Found: 591.2 (M+H+).

Quelle