Реакция #70514

Уравнение реакции

isopropyl alcohol

6-bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

1H-indol-4-ylboronic acid

sodium hydrogen carbonate

→

title compound

6-(1H-Indol-4-yl)-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

Растворители

ethyl acetate

water

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixtures
2. 2
   ФильтрацияThe mixture was filtered
3. 3
   Другоеthe organic layer collected
4. 4
   ПромывкаThe organic layer was washed with water
5. 5
   СушкаThe organic layer was dried over magnesium sulphate
6. 6
   Фильтрацияfiltered
7. 7
   Другоеsolvent removed in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
9. 9
   Другоеpre-absorbed onto silica
10. 10
    ДругоеPurification
11. 11
    ДругоеThe desired fractions were collected
12. 12
    Другоеsolvent removed in vacuo

Методика

Five reactions were set up with 6-bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (500 mg, 1.53 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (125 mg, 0.153 mmol), 1H-indol-4-ylboronic acid (370 mg, 2.3 mmol), saturated aqueous sodium hydrogen carbonate (3 ml) and isopropyl alcohol (12 ml) in each. They were all heated at 150° C. for 10 minutes in the microwave. The reaction mixtures were combined and water (250 ml) and ethyl acetate (250 ml) added. The mixture was filtered and the organic layer collected. The organic layer was washed with water followed by brine. The organic layer was dried over magnesium sulphate, filtered and solvent removed in vacuo. The residue was dissolved in dichloromethane and pre-absorbed onto silica. Purification was carried out using chromatography on silica eluting with 0-25% ethyl acetate in cyclohexane. The desired fractions were collected and combined and solvent removed in vacuo to give the title compound as a yellow solid (1.72 g).

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