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Sodium Carbonate → 1h-Indole-3-acetic acid,2-phenyl-,ethyl ester

HRID 2187630
ノート
印刷プレビュー

反応式

HRID 2187630 の反応式
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(=O)([O-])[O-].[Na+].[Na+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]1([C:2]2[NH:3][C:4]3[C:9]([C:10]=2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 53994886Ethyl (2-bromo-1H-indol-3-yl)acetate

生成物 1

HCID 125026691h-Indole-3-acetic acid,2-phenyl-,ethyl ester収率 81%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

To a solution of 2.0 g (7.1 mmol) of ethyl (2-bromoindol-3-yl)acetate in 40 ml of dioxane was added under argon 1.2 g (0.11 mmol) of Pd(PPh3)4 and 13.3 ml of 2.0 M sodium carbonate. After stirring at room temperature for ca. 15 min, 1.3 g (11 mmol) of benzeneboronic acid was added, and the mixture was heated at 80° C. under argon overnight. The mixture was cooled to room temperature and solids were removed by filtration. The filtrate was concentrated and chromatographed on silica gel with toluene as an eluent to yield 1.6 g (81%) of the 2-phenyl indole as a yellow crystalline solid.

後処理

  1. temperaturethe mixture was heated at 80° C. under argon overnight
  2. temperatureThe mixture was cooled to room temperature
  3. customsolids were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on silica gel with toluene as an eluent

出典と根拠

ORDレコード
ord-fd2b2434d51e4ab8bdf44da49d132eb7
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06410562B1

反応ノート

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