Potassium Phosphate, Tribasic → 5-(4-Cyclohexylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 646132Notes

Reaction equation

HRID 646132 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:56]1([C:62]2[CH:67]=[CH:66][C:65](B(O)O)=[CH:64][CH:63]=2)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1.C([O-])(O)=O.[Na+]>CCO.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:59]1[CH:58]=[CH:57][C:56]([CH:62]3[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]3)=[CH:61][CH:60]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 516892Sodium BicarbonateHCID 45891894-Cyclohexylbenzeneboronic acidHCID 687002455-Bromo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

Product 1

HCID 686997835-(4-Cyclohexylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterYield 93%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (154 mg, 0.38 mmol), K3PO4 (282 mg, 1.83 mmol), Pd(OAc)2 (4.5 mg, 0.02 mmol), tri(o-tolyl)phosphine (12 mg, 0.04 mmol), and toluene (3.5 mL) was stirred under argon for 25 min at room temperature. 4-Cyclohexylphenylboronic acid (117 mg, 0.57 mmol) in EtOH (0.5 mL) was added and the mixture was heated at reflux for 1 h. The mixture was allowed to cool, poured into NaHCO3 (aq. sat.), and extracted wait EtOAc. The combined extracts were washed with brine, dried over Na2SO4, concentrated and purified by chromatography to give the sub-title compound (170 mg, 93%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureto cool
  4. extractionextracted
  5. waitwait EtOAc
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by chromatography

Sources & evidence

ORD record
ord-5c8d24a2873540c4a443981c151a4e78
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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