Reaktion #1703425

Reaktionsgleichung

5-Chloro-1-(2,2-dimethylpropyl)-3-(prop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Cs2CO3

2-[4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-2-ol

→

1-(2,2-dimethylpropyl)-5-[5-(1-hydroxy-1-methylethyl)-2-methylphenyl]-3-prop-2-en-1-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

1-(2,2-Dimethylpropyl)-5-[5-(1-hydroxy-1-methylethyl)-2-methylphenyl]-3-prop-2-en-1-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Lösungsmittel

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction contents
2. 2
   Filtrationwere filtered through Celite®
3. 3
   Waschenwashed with EtOAc (5 mL)
4. 4
   workup.ADDITIONThe filtrate was then diluted with saturated aqueous NaHCO3 (5 mL)
5. 5
   SonstigeThe layers were separated
6. 6
   Extraktionthe aqueous layer was back-extracted with 3×5 mL EtOAc
7. 7
   TrocknenThe combined organics were dried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto give a brown semi-solid
11. 11
    SonstigePurification by reverse-phase HPLC

Vorschrift

5-Chloro-1-(2,2-dimethylpropyl)-3-(prop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-5, 100 mg, 0.36 mmol, 1.0 equiv), Cs2CO3 (1.17 g, 3.57 mmol, 10.0 equiv), 2-[4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-2-ol (225 mg, 0.82 mmol, 2.3 equiv), and bis(tri-t-butyl-phosphino)palladium (18.3 mg, 0.04 mmol, 0.1 equiv) were added to anhydrous NMP (4 mL). The resulting suspension was warmed to 100° C. for 20 min in a microwave emitter. Following this duration, the reaction contents were filtered through Celite® and washed with EtOAc (5 mL). The filtrate was then diluted with saturated aqueous NaHCO3 (5 mL). The layers were separated and the aqueous layer was back-extracted with 3×5 mL EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated to give a brown semi-solid. Purification by reverse-phase HPLC afforded 1-(2,2-dimethylpropyl)-5-[5-(1-hydroxy-1-methylethyl)-2-methylphenyl]-3-prop-2-en-1-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-6) as a white solid. HRMS (M+H)+: observed=394.2490, calculated=394.2489.

Quelle