Реакция #2146787

Уравнение реакции

[6-Methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone

potassium carbonate

ethyl bromoacetate

→

title compound

Выход 98.0%

{4-[6-Methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester

Выход 98.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling to room temperature the reaction mixture
2. 2
   Другоеwas quenched with 10% NH4Cl(aq) (20 mL)
3. 3
   Экстракцияextracted with ethyl acetate (30 mL)
4. 4
   ДругоеThe organic layer was separated
5. 5
   Промывкаwashed with water (3×10 mL) and brine (10 mL)
6. 6
   Сушкаdried over magnesium sulphate
7. 7
   Другоеthe solvent removed under reduced pressure
8. 8
   ДругоеThe crude residue was purified by flash column chromatography (silica gel, eluent=2:1 hexane:ethyl acetate)

Методика

To a stirred solution of [6-Methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (45 mg, 0.091 mmol) and potassium carbonate (40 mg, 0.29 mmol) in dry DMF (2.5 mL) was added ethyl bromoacetate (30 μL, 0.27 mmol) and the reaction heated to 70° C. for 2 h. After cooling to room temperature the reaction mixture was quenched with 10% NH4Cl(aq) (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated and washed with water (3×10 mL) and brine (10 mL), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, eluent=2:1 hexane:ethyl acetate) to give the title compound as a yellow solid (44 mg, 98%). 1H-NMR (CDCl3) δ 8.28 (s, 1H), 8.06 (s, 1H), 7.13 (s, 2H), 7.10 (d, J=8.7 Hz, 1H), 7.04 (d, J=2.1 Hz, 1H), 6.79 (dd, J=8.7, 2.1 Hz, 1H), 4.91 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 3.77 (s, 6H), 1.27 (t, J=7.1 Hz, 3H).

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