تفاعل #1710677

معادلة التفاعل

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

المذيبات

1,2-dimethoxyethane

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر