反应详情

3-(2-Chloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (3, 564 mg, 2.5 mmol) and 4-aminophenylboronic acid, pinacol ester (602 mg, 2.75 mmol) are dissolved in toluene (25 mL) and EtOH (15 mL). A 2M solution of Na2CO3 is added (5 mL) and the mixture is degassed by leading a stream of nitrogen through the solution. Tetrakis(triphenylphosphine) palladium is added (144 mg, 5 mol %) and the mixture is heated under reflux for 48 hours. The mixture is diluted with EtOAc, washed with saturated NaHCO3, the organic phase is dried (MgSO4), filtered, and concentrated. The mixture is purified by silica gel chromatography using a gradient of ethyl acetate in hexanes (40-100%) to give 576 mg (2.04 mmol, 82%) of 4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)pyrimidin-2-yl]aniline. RT 1.51, M+H=283.1

1. customthe mixture is degassed
2. additionTetrakis(triphenylphosphine) palladium is added (144 mg, 5 mol %)
3. temperaturethe mixture is heated
4. temperatureunder reflux for 48 hours
5. additionThe mixture is diluted with EtOAc
6. washwashed with saturated NaHCO3
7. dry with materialthe organic phase is dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe mixture is purified by silica gel chromatography