Potassium Carbonate → methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1807629Notes

Reaction equation

HRID 1807629 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 67225298methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (1, 6.14 g, 18.3 mmol), 2-(benzyloxy)phenylboronic acid (5.00 g, 21.9 mmol) and potassium carbonate (5.80 g, 42 mmol) in 450 mL of 1,2-dimethoxyethane/water (4:1) was thoroughly flushed with argon. Then trans-BIS(triphenylphosphine)palladium(II) chloride (0.641 g, 0.91 mmol) was added and the reaction was heated at 70° C. under argon for 12 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethylacetate (AcOEt). Combined organic layers were washed with a saturated solution of NaHCO3 and brine, dried over anhydrous Na2SO4 and filtered. The filtered solution was concentrated under vacuum to give methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate 2: m/z=440 (M+H)+. Step 2

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethylacetate (AcOEt)
  3. washCombined organic layers were washed with a saturated solution of NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtered solution was concentrated under vacuum

Sources & evidence

ORD record
ord-cf0089db8a32452b925bc624b92051e4
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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