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

HRID 420970
ノート
印刷プレビュー

反応式

HRID 420970 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-dc38b2cd4cdd43f7ae3fef4ec38c58ce
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097623B2

反応ノート

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