Water → HCID 68309093, compound

HRID 922476Notes

Reaction equation

HRID 922476 reaction equation
Cl[C:2]1[C:7]2[C:8]([CH3:16])=[CH:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH3:18])[N:3]=1.[CH3:20]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O>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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[CH3:15][O:14][CH2:13][CH2:12][CH2:11][N:10]1[C:6]2[CH:5]=[C:4]([C:17](=[O:19])[CH3:18])[N:3]=[C:2]([CH3:20])[C:7]=2[C:8]([CH3:16])=[CH:9]1

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 88931009HCID 88931009, compound

Product 1

HCID 68309093HCID 68309093, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[4-chloro-1-(3-methoxypropyl)-3-methyl-1H-pyrrolo[3,2-c]pyridin-6-yl]ethanone (50 mg) in 1,4-dioxane (2 mL) were added trimethylboroxine (50 μL), cesium carbonate (174 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (17 mg) and tris(dibenzylideneacetone)dipalladium (8 mg) under argon, and the mixture was stirred at 80° C. for 2 hours. The reaction solution was cooled, and then thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=1/1) to give 1-[1-(3-methoxypropyl)-3,4-dimethyl-1H-pyrrolo[3,2-c]pyridin-6-yl]ethanone [REx(105-9)] (105 mg) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-b039894465e243b3bf2eb6a50b33123f
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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