Реакция #327360

Уравнение реакции

1-methylindole-5-boronic acid pinacol ester

3-bromoaniline

K3PO4

PCy3

→

3-(1-methyl-1H-indol-5-yl)-phenylamine

Выход 46.0%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was refluxed overnight under argon flow
2. 2
   ДругоеThe solvent was removed under vacuum
3. 3
   СушкаThe organic phase was dried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under vacuum
6. 6
   ДругоеThe crude product was purified by flash silica column chromatography (5-60% EtOAc/hexanes)
7. 7
   ДругоеThe purification
8. 8
   ДругоеThe solvent was removed under vacuum from fractions
9. 9
   workup.ADDITIONcontaining product
10. 10
    Другоеresulting in 0.059 g in 46% yield

Методика

1-methylindole-5-boronic acid pinacol ester (0.224 g, 0.872 mmol) and 3-bromoaniline (0.063 mL, 0.581 mmol) were combined in dioxane (2 mL) in a flame-dried, round-bottom flask. K3PO4 (1.27M, 0.778 mL, 0.99 mmol), PCy3 (0.004 g, 0.014 mmol), and Pd2(dba)3 (0.005 g, 0.006 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in CH2Cl2. The organic phase was dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by flash silica column chromatography (5-60% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.059 g in 46% yield.

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