Ethanol → 5-Phenyloxindole

HRID 49121

反応式

HRID 49121 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:21]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 6111935-Bromo-2-oxindole

生成物 1

HCID 133019785-Phenyloxindole収率 77.3%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

5-Bromo-2-oxindole (5 g, 23.5 mmol) was dissolved in 110 mL of toluene and 110 mL of ethanol with stirring and a little heating. Tetrakis(triphenylphosphine)-palladium(0) (1.9 g, 1.6 mmol) was added followed by a 2M aq. solution of sodium carbonate (40 mL, 80 mmol). To this mixture benzene boronic acid (3.7 g, 30.6 mmol) was added and the mixture was heated in a 100° C. oil bath. After 12 h, the reaction was diluted with ethyl acetate (500 mL), washed with saturated aq. sodium bicarbonate (200 mL), water (200 mL), 1N HCl (200 mL) and brine (200 mL). The organic layer was dried with magnesium sulfate and concentrated to afford a brown solid. Trituration with dichloromethane and filtering afforded 3.8 g (77%) of a tan solid.

後処理

  1. washwashed with saturated aq. sodium bicarbonate (200 mL), water (200 mL), 1N HCl (200 mL) and brine (200 mL)
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated
  4. customto afford a brown solid
  5. filtrationTrituration with dichloromethane and filtering

出典と根拠

ORDレコード
ord-53c59fa6a8fe410f8728af630b8a9eb8
出典データセット
uspto-grants-2004_03
特許番号
US06706709B2

関連ノート

読み込み中…