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

HRID 2187630
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HRID 2187630 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 31275
1,4-Dioxane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd2b2434d51e4ab8bdf44da49d132eb7
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06410562B1

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