Reacción #43792

Ecuación de reacción

7-(benzyloxy)-6-methoxyquinolin-4(1H)-one

Cs2CO3

3,4-difluoronitrobenzene

→

product

Rendimiento 46.0%

7-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

Rendimiento 46.0%

Disolventes

DMF

CH3CN

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred at rt overnight
2. 2
   workup.ADDITIONa mixture of O- and N-alkylation products
3. 3
   ConcentraciónIt was mostly concentrated in vacuo, EtOAc (200 mL) and water (50 mL)
4. 4
   workup.ADDITIONwere added to the residue, EtOAc layer
5. 5
   Otrowas separated
6. 6
   Secadodried over MgSO4
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue was purified by flash column chromatography on silica gel eluting with hexane

Procedimiento

A mixture of 7-(benzyloxy)-6-methoxyquinolin-4(1H)-one (4.4 g, 15.6 mmol), Cs2CO3 (9.0 g) in DMF (40 mL) and CH3CN (40 mL) was stirred for 30 minutes at rt. To this mixture was added 3,4-difluoronitrobenzene (2.5 g, 15.7 mmol), and the reaction mixture was stirred at rt overnight. The reaction product was a mixture of O- and N-alkylation products. It was mostly concentrated in vacuo, EtOAc (200 mL) and water (50 mL) were added to the residue, EtOAc layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with hexane:EtOAc:MeOH/800:200:40, and then 700:300:40 to obtain the desired O-alkylation product (3.0 mg, 46%) as a white solid. 1H NMR (CDCl3) δ 8.73 (d, 1H, J=6.0 Hz), 8.29-8.26 (m, 2H), 8.08 (s, 1H), 7.60-7.35 (m, 7H), 6.67 (d, 1H, J=6.6 Hz), 5.42 (s, 2H), 4.10 (s, 3H); MS(ESI+) m/z 421.3 (M+H)+.

Fuente