Cesium carbonate → HCID 59259721, compound

HRID 642970Notes

Reaction equation

HRID 642970 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[Cs+].[Cs+].[N:18]1([CH2:24][CH2:25][O:26][CH2:27][B-](F)(F)F)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.O1CCOCC1>[N:18]1([CH2:24][CH2:25][O:26][CH2:27][C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 214133-BromoquinolineHCID 634876Binap, (A+-)-HCID 49761724HCID 49761724, compound

Product 1

HCID 59259721HCID 59259721, compoundYield 3.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-bromoquinoline (80 mg, 0.39 mmol) and 1,4-dioxane (4 ml) were added water (0.4 ml), cesium carbonate (564 mg, 1.7 mmol), [(2-morpholin-4-ylethoxy)-methyl]trifluoroborate (145 mg, 0.58 mmol), palladium (II) acetate (8.6 mg, 0.04 mmol) and 2,2′-bis(diphenylphosphino)1,1′-binaphthyl (48 mg 0.08 mmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 15 hours. After the reaction mixture was cooled at room temperature, water and ethyl acetate were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:2) to obtain the title compound (3.2 mg, 0.01 mmol, 3.1%).

Workup

  1. temperatureAfter the reaction mixture was cooled at room temperature
  2. filtrationfollowed by filtration
  3. washThe separated organic layer was washed with an aqueous saturated sodium chloride solution
  4. customThe organic layer was separated
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-dbee206eb4ab4e4c9a77ccbf2c1f7457
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Reaction notes

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