تفاعل #1053259
ord-f8d1b962b31a4481803ba2f5dd522aab
معادلة التفاعل
المتفاعلات
ظروف التفاعل
المعالجة
- 1درجة الحرارةcooled to room temperature
- 2أخرىThe liquid was separated from the solid residue
- 3غسيلthe residue was rinsed with dichloromethane, which
- 4أخرىThe solvent was evaporated
- 5أخرىthe crude product was partitioned between brine (˜4 mL) and dichloromethane (˜4 mL)
- 6غسيلThe organic layer was washed with additional brine
- 7تجفيفdried over magnesium sulfate
- 8ترشيحfiltered
- 9أخرىThe solvent was evaporated
- 10أخرىthe residue, an orange oil, was purified by column chromatography (hexane/ethyl acetate)
الإجراء التجريبي
To a reaction flask charged with 10.8 mg (0.0094 mmol) of tetrakis(triphenylphosphine)palladium(0) in ethylene glycol dimethyl ether (1.8 mL) under nitrogen was added 107 mg (0.24 mmol) of the product from Example 6. The resulting yellow solution was stirred for 15 min before the addition of 34.0 mg (0.28 mmol) of pyridine-3-boronic acid dissolved in ethanol (0.4 mL) and ethylene glycol dimethyl ether (0.2 mL), and the subsequent addition of 0.23 mL (0.47 mmol) of a 2 M sodium carbonate aqueous solution. The reaction mixture was heated at 80° C. for ˜20 h and then cooled to room temperature. The liquid was separated from the solid residue, and the residue was rinsed with dichloromethane, which was subsequently combined with the isolated liquid. The solvent was evaporated, and the crude product was partitioned between brine (˜4 mL) and dichloromethane (˜4 mL). The organic layer was washed with additional brine, dried over magnesium sulfate, and filtered. The solvent was evaporated, and the residue, an orange oil, was purified by column chromatography (hexane/ethyl acetate) to yield 35 mg (36%) of the title compound.