Ethanol → 6-Pyridin-3-yl-1,3-dihydro-indol-2-one

HRID 1790979

反応式

HRID 1790979 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)(O)CC.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=[O:11])[NH:8]3)=[CH:4][CH:3]=2)[CH:27]=1

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneHCID 69587225Pyridine-3-boronic acid propane diol

生成物 1

HCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-one収率 42%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL of toluene and 60 mL of ethanol with stirring and a little heating tetrakis(triphenyl-phosphine)palladium(0) (2.3 g, 1.9 mmol) was added followed by a 2 M aqueous solution of sodium carbonate (50 mL, 100 mmol) and pyridine-3-boronic acid propane diol (5 g, 30.7 mmol). The mixture was heated in a 100° C. oil bath for 12 hours. The cooled reaction was diluted with ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried with magnesium sulfate and concentrated to afford a brown solid. The residue was triturated with methylene chloride/diethyl ether to give 2.32 g (42%) of 6-pyridin-3-yl-1,3-dihydro-indol-2-one as a brown solid.

後処理

  1. additionwas added
  2. customThe cooled reaction
  3. washwashed with saturated aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customto afford a brown solid
  7. customThe residue was triturated with methylene chloride/diethyl ether

出典と根拠

ORDレコード
ord-5a35eb37090d4673953f933d414f1791
出典データセット
uspto-grants-2006_07
特許番号
US07071332B2

関連ノート

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