Реакция #52692

Уравнение реакции

sodium carbonate

3-(3-bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one

naphthalene-2-boronic acid

→

3-(4,5-dimethoxy-2-naphthalen-2-ylbenzylidene)-1,3-dihydroindol-2-one

Выход 30.9%

Растворители

toluene

ethanol

Условия реакции

Обработка

1. 1
   ДругоеThe precipitate which formed
2. 2
   Фильтрацияwas filtered
3. 3
   Промывкаwashed with ethanol
4. 4
   workup.DISSOLUTIONdissolved in 20% methanol/toluene
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe resulting solid was triturated with hexanes
8. 8
   Другоеdried

Методика

Tetrakis(triphenylphosphine)palladium (0) (0.02 g) was added to a solution of 3-(3-bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one (0.20 g) in toluene (1 ml) and ethanol (1 ml) followed by addition of 2M aqueous sodium carbonate (1.1 ml). To this mixture was added naphthalene-2-boronic acid (0.11 g), and the mixture was held at 100° C. in a sealed tube for 12 hours. The precipitate which formed was filtered, washed with ethanol and then dissolved in 20% methanol/toluene, filtered and concentrated. The resulting solid was triturated with hexanes and dried to afford 0.07 g (29%) of 3-(4,5-dimethoxy-2-naphthalen-2-ylbenzylidene)-1,3-dihydroindol-2-one as an orange solid.

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