Reaktion #641796

Reaktionsgleichung

2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzaldehyde

potassium carbonate

EtOAc

3,5-dibromo-2-methoxy-pyridine

→

2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzaldehyde

Lösungsmittel

DME

H2O

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was purged with N2 for 30 minutes
2. 2
   Temperaturcooled to room temperature
3. 3
   TrocknenThe combined organic layers were dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigethe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Vorschrift

2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzaldehyde (1.59 g, 4.4 mmol), 3,5-dibromo-2-methoxy-pyridine (1.19 g, 4.4 mmol), and potassium carbonate (2.17 g, 15.6 mmol) were combined in DME (13 mL) and H2O (6 mL). The solution was purged with N2 for 30 minutes, and dichlorobis(triphenylphosphine)palladium(II) (0.156 g, 0.22 mmol) was added. The reaction was stirred at 85° C. overnight, and then cooled to room temperature and worked-up with EtOAc and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give 2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzaldehyde, which was repurified by preparative HPLC.

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