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Potassium Phosphate, Tribasic → Ethyl 5-(4-(trifluoromethyl)phenyl)-1H-indole-2-carboxylate

HRID 420970
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HRID 420970 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(O)=O.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.CCO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:21]1[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]
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참가 물질

9

반응물 5

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 516892Sodium BicarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 57419913Ethyl 5-(4-(trifluoromethyl)phenyl)-1H-indole-2-carboxylate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

A mixture of 5-bromoindole-2-carboxylic acid ethyl ester (4.22 g, 16 mmol), 4-trifluoromethylphenylboronic acid (4.50 g, 24 mmol), K3PO4 (11.7 g, 55 mmol), Pd(OAc)2 (176 mg, 0.78 mmol), tri-o-tolylphosphine (478 mg, 1.6 mmol), EtOH (20 mL) and toluene (90 mL) was stirred under argon for 20 min at rt, heated at 100° C. for 2 h, cooled and poured into NaHCO3 (aq, sat). The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 3.91 g (75%).

후처리

  1. temperatureheated at 100° C. for 2 h
  2. temperaturecooled
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined extracts were washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by chromatography

출처 및 근거

ORD 기록
ord-dc38b2cd4cdd43f7ae3fef4ec38c58ce
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097623B2

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