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

HRID 420970Notes

Reaction equation

HRID 420970 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-dc38b2cd4cdd43f7ae3fef4ec38c58ce
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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