تفاعل #69467
ord-6c347fd2053c4b53bdc6763a8606b949
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1أخرىwas bubbled with nitrogen for 10 minutes
- 2أخرىthe mixture bubbled with nitrogen for 2 minutes
- 3درجة الحرارةUpon cooling to room temperature the mixture
- 4أخرىwas partitioned between DCM (500 mL) and water (250 mL)
- 5غسيلThe organic phase was washed with brine
- 6تجفيفdried with magnesium sulfate
- 7ترشيحfiltered
- 8تركيزconcentrated under reduced pressure
- 9أخرىto give a brown gum
- 10أخرىThe gum was purified by flash column chromatography on silica using gradient elution (0% methanol/DCM to 5% methanol/DCM)
الإجراء التجريبي
6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one (296 g, 716 mmol), 1-bromo-3,5-difluorobenzene (173 g, 895 mmol) and cesium carbonate (700 g, 2148 mmol) suspended in dioxane (3 L) was bubbled with nitrogen for 10 minutes. diacetoxypalladium (8.04 g, 36 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (41.4 g, 72 mmol) were added and the mixture bubbled with nitrogen for 2 minutes then heated at 100° C. for 2 hours. Upon cooling to room temperature the mixture was partitioned between DCM (500 mL) and water (250 mL). The organic phase was washed with brine and dried with magnesium sulfate, filtered and concentrated under reduced pressure to give a brown gum. The gum was purified by flash column chromatography on silica using gradient elution (0% methanol/DCM to 5% methanol/DCM). The desired product, 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one (282 g, 75%), was thus isolated as a pale yellow dry film. Mass Spectrum: m/z [M+H]+=526. More material was made by repeating this reaction.