Potassium Phosphate, Tribasic → HCID 68310563, compound

HRID 922441Notes

Reaction equation

HRID 922441 reaction equation
Cl[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:27]B1OB(C)OB(C)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:18][O:17][CH2:16][CH2:15][CH2:14][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11](=[O:13])[CH3:12])[CH:6]=2)[C:2]([CH3:27])=[CH:3]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 574072TrimethylboroxineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 68308664HCID 68308664, compound

Product 1

HCID 68310563HCID 68310563, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-[3-chloro-1-(3-methoxypropyl)-1H-indol-6-yl]ethanone (843 mg) in 1,4-dioxane (15 mL) were added potassium phosphate (1.35 g), trimethylboroxine (883 mg), tris(dibenzylideneacetone)dipalladium (290 mg) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (605 mg) under argon, and the mixture was heated to stir at 110° C. for 4 hours. Thereto was added water under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1→3/2) to give 1-[1-(3-methoxypropyl)-3-methyl-1H-indol-6-yl]ethanone [REx(9-1)] (663 mg) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1→3/2)

Sources & evidence

ORD record
ord-cd2bbe60256c45ccbea11259e33a23ad
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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