반응 #327360

반응 방정식

1-methylindole-5-boronic acid pinacol ester

3-bromoaniline

K3PO4

PCy3

→

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

수율 46.0%

용매

dioxane

반응 조건

후처리

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

실험 절차

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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