Reaction #7078

Reaction equation

ammonium chloride

5-Bromo-3-methyl-1,3-dihydro-indol-2-one

3-nitrophenyl boronic acid

potassium carbonate

→

title compound

Yield 60.3%

5-bromo-3-methyl-indol-2-one

Yield 60.3%

Solvents

water

dimethoxyethane

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureto reflux for 8 h
3. 3
   Extractionand the aqueous layer was extracted with EtOAc (×3)
4. 4
   DryingThe combined organic layers were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by column chromatography (SiO2, EtOAc: hexane 1:2)
8. 8
   Washeluted

Procedure

5-Bromo-3-methyl-1,3-dihydro-indol-2-one (0.50 g, 2.22 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.15 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (18 cm3). After 15 min., 3-nitrophenyl boronic acid (0.74 g, 4.45 mmol) was added, followed by potassium carbonate (1.86 g, 13.5 mmol) in water (7 cm3). The reaction was heated to reflux for 8 h and then stirred at room temperature overnight. Saturated ammonium chloride was added; and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography (SiO2, EtOAc: hexane 1:2); eluted: 2:1 hexane; ethyl acetate, to give the title compound (0.30 g, 47%), mp 200–203° C.; 1H NMR (DMSO-d6) δ 1.41 (d, 3H, J=7.61 Hz), 3.50 (q, 1H, J=7.60 Hz), 6.96 (d, 1H, J=8.08 Hz), 7.62 (d, 1H, J=8.06 Hz), 7.75–7.70 (m, 2H), 8.18–8.10 (m, 2H), 8.41–8.39 (m, 1H), 10.5 (s, 1H); IR (KBr) 3450, 1700 cm−1; MS (EI) m/z 267 (M−H); Anal. Calc. for C15H12N2O3+0.2C4H8O2: C, 66.61; H, 4.46; N, 9.83; Found: C, 66.26; H, 4.59; N, 10.06.

Source