Potassium Carbonate → tert-butyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

HRID 1807639Notes

Reaction equation

HRID 1807639 reaction equation
Br[C:2]1[N:3]([CH3:24])[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][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=2.[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.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>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:7][CH:8]=3)[N:3]([CH3:24])[C:2]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[OH:25])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 58317838tert-butyl 2-bromo-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate

Product 1

HCID 58317805tert-butyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl 2-bromo-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate (24, 500 mg, 1.27 mmol), 2-hydroxy-phenylboronic acid (211 mg, 1.53 mmol) and potassium carbonate (1.35 g, 12.74 mmol) in 100 mL of 1,2-dimethoxyethane/water (4:1) was thoroughly flushed with argon. Then trans-bis(triphenylphosphine)palladium(II) chloride (0.147 g, 0.127 mmol) was added and the reaction was heated at 100° C. under argon for 12 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethylacetate (EtOAc). 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 tert-butyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate 25: m/z=406 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethylacetate (EtOAc)
  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-f5f204677b904f8aa7bea7e471e8c968
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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