Potassium Carbonate → HCID 58525635, compound

HRID 1894980Notes

Reaction equation

HRID 1894980 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2.[CH2:16](B(O)O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH2:16]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 65389Phenylethane Boronic AcidHCID 53465709Methyl 6-bromoquinoline-3-carboxylate

Product 1

HCID 58525635HCID 58525635, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a 2-5 mL microwave vial fitted with a stirbar was added methyl 6-bromoquinoline-3-carboxylate (0.25 g, 0.94 mmol), phenethylboronic acid (0.282 g, 1.88 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.0773 g, 0.094 mmol), and potassium carbonate (0.39 g, 2.82 mmol). The vial was capped and 1,4-dioxane (4 mL) and water (1 mL). The contents of the vial were heated in a microwave at 130° C. for 0.5 h. The vial was cooled to room temperature and opened. The contents were partitioned between ethyl acetate and water. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (hexanes to 75/25 hexanes/ethyl acetate gradient) to afford the desired product (0.125 g, 36%). LC-MS: (FA) ES+ 292.

Workup

  1. customTo a 2-5 mL microwave vial fitted with a stirbar
  2. customThe vial was capped
  3. temperatureThe vial was cooled to room temperature
  4. customThe contents were partitioned between ethyl acetate and water
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude residue was purified by silica gel chromatography (hexanes to 75/25 hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-5ab887a086d840f3883630d2358cce0d
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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