Reaktion #57214

Reaktionsgleichung

9-borabicyclo[3.3.1]nonane

tetrahydrofuran

4-[3-(4-nitrophenyl)-1-(2-propen-1-yl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

tetrahydrofuran

→

title compound

Ausbeute 84.0%

3-{3-(4-nitrophenyl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-1-yl}-1-propanol

Ausbeute 84.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturre-cooled to 0° C.
2. 2
   Sonstigeby quenching with water (1.7 mL)
3. 3
   workup.STIRRINGAfter 15 minutes of stirring at 0° C.
4. 4
   workup.ADDITION6N aqueous sodium hydroxide (1.24 mL) was added dropwise
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 1.5 h at 0° C.
6. 6
   Einengenconcentrated in vacuo
7. 7
   workup.ADDITIONWater (10 mL) was added to the residue
8. 8
   Extraktionthe solution extracted with ethyl acetate (3×15 mL)
9. 9
   Trocknenthe combined organic layers dried over magnesium sulfate
10. 10
    Einengenconcentrated in vacuo

Vorschrift

To a solution of 0.5M 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (6.16 mL) cooled to 0° C. was added a solution of 4-[3-(4-nitrophenyl)-1-(2-propen-1-yl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.06 mmol) in tetrahydrofuran (14 mL). The reaction mixture was stirred at room temperature under an inert atmosphere for 4.5 h and then re-cooled to 0° C. followed by quenching with water (1.7 mL). After 15 minutes of stirring at 0° C., 6N aqueous sodium hydroxide (1.24 mL) was added dropwise followed by 30% aqueous hydrogen peroxide (0.865 mL). The reaction mixture was stirred for 1.5 h at 0° C., neutralized with 6N aqueous hydrochloric acid and concentrated in vacuo. Water (10 mL) was added to the residue and the solution extracted with ethyl acetate (3×15 mL), the combined organic layers dried over magnesium sulfate and concentrated in vacuo to afford the title compound (84%). ESMS [M+H]+: 504.2

Quelle