반응 #1710677

반응 방정식

sodium carbonate

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

5-methyl-3-pyridinyl boronic acid

→

1-methyl-5-(5-methyl-pyridin-3-yl)-1,3-dihydro-indol-2-one

용매

1,2-dimethoxyethane

dichloromethane

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed
2. 2
   workup.ADDITIONwas added
3. 3
   기타The reaction vessel was sealed
4. 4
   온도The reaction mixture was cooled to room temperature
5. 5
   여과filtered through glass wool
6. 6
   workup.ADDITIONThe filtrate was further diluted with saturated aqueous sodium bicarbonate
7. 7
   기타the layers were separated
8. 8
   추출The aqueous layer was extracted two times with dichloromethane
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated
12. 12
    기타The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 6%)

실험 절차

To 5-bromo-1-methyl-1,3-dihydro-indol-2-one (CAS#20870-90-0, 80 mg, 0.35 mmol) was added 5-methyl-3-pyridinyl boronic acid (CAS#173999-18-3, 55 mg, 0.39 mmol), in 1,2-dimethoxyethane (2.7 mL) and 2 M aqueous sodium carbonate (0.45 mL, 0.9 mmol). The reaction mixture was degassed and placed under an argon atmosphere, at which time resin bound tetrakis(triphenylphosphine)palladium(0), specifically polystyrene triphenylphosphine palladium (0) [PS—PPh3-Pd(0) (Biotage), 0.09 mmol/g loading, (195 mg, 0.018 mmol)] was added. The reaction vessel was sealed and was heated by microwave irradiation at 100° C. for 1.5 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane and filtered through glass wool. The filtrate was further diluted with saturated aqueous sodium bicarbonate and the layers were separated. The aqueous layer was extracted two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 6%) to afford 1-methyl-5-(5-methyl-pyridin-3-yl)-1,3-dihydro-indol-2-one; HRMS: (ESI) m/z 239.1181 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 2.42 (s, 3H), 3.27 (s, 3H), 3.61 (s, 2H), 6.93 (d, J=8.1 Hz, 1H), 7.45-7.58 (m, 2H), 7.67 (s, 1H), 8.42 (s, 1H), 8.63 (s, 1H).

출처