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

HRID 646167Notes

Reaction equation

HRID 646167 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1Cl)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.[Cl:56][C:57]1[CH:62]=[CH:61][C:60](B(O)O)=[CH:59][CH:58]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:60]1[CH:61]=[CH:62][C:57]([Cl:56])=[CH:58][CH:59]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 686966545-Bromo-3-chloro-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester2×

Product 1

HCID 687014075-(4-Chlorophenyl)-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl esterYield 35%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-3-chloro-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester (see Example 35(b) 402 mg, 1.0 mmol), K3PO4 (716 mg, 3.37 mmol), Pd(OAc)2 (22 mg, 0.1 mmol) and biphenyl-2-yldi-tert-butylphosphine (53 mg, 0.18 mmol) in toluene (10 mL) was stirred at ambient temperature for 10 min after which 4-chlorophenyl boronic acid (233 mg, 1.49 mmol) was added. The reaction was heated at reflux for 5 h, cooled to room temperature and filtered. The filter cake was washed with toluene (5 mL), the combined filtrates were concentrated and the residue was purified by chromatography to afford the sub-title compound (150 mg, 35%).

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 5 h
  4. filtrationfiltered
  5. washThe filter cake was washed with toluene (5 mL)
  6. concentrationthe combined filtrates were concentrated
  7. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-bf86c61d7e194cfc9fbf10ecc9d91c7a
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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