Sodium Carbonate → HCID 22482418, compound

HRID 2181713Notes

Reaction equation

HRID 2181713 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][CH3:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(B(CC)[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:12]([C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH:11]=2)[CH3:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 22482430HCID 22482430, compound

Product 1

HCID 22482418HCID 22482418, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a well-stirred mixture consisting of the title compound of Step 1, this Example (1.40 g, 5.93 mmol), diethyl(3-pyridyl)borane (0.96 g, 6.53 mmol) and bis(triphenylphosphine) palladium (II) chloride (458 mg, 0.65 mmol) in tetrahydrofuran (15 ml), a 7.5 ml aqueous solution of sodium carbonate (2.51 g, 23.7 mmol) was added. The reaction mixture was then stirred at 90° C. for 5 hours, and then at ambient temperature for 18 hours. The aqueous phase of the biphasic reaction mixture is separated and extracted with an equal volume of ethyl acetate. The solvent of the organic phase of the reaction mixture was removed in vacuo and the residue is extracted with ethyl acetate (25 ml). The combined organic extracts are dried (anhydrous sodium sulfate) and concentrated in vacuo, yielding a dark viscous oil. Flash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with ethyl acetate) afford the title compound (807 mg, 58% yield) as a viscous yellow syrup.

Workup

  1. waitat ambient temperature for 18 hours
  2. customThe aqueous phase of the biphasic reaction mixture
  3. customis separated
  4. extractionextracted with an equal volume of ethyl acetate
  5. customThe solvent of the organic phase of the reaction mixture was removed in vacuo
  6. extractionthe residue is extracted with ethyl acetate (25 ml)
  7. dry with materialThe combined organic extracts are dried (anhydrous sodium sulfate)
  8. concentrationconcentrated in vacuo
  9. customyielding a dark viscous oil
  10. washFlash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with ethyl acetate)

Sources & evidence

ORD record
ord-9363e74361a24744bee5c5fe2b63313e
Source dataset
uspto-grants-2005_05
Patent number
US06894062B1

Reaction notes

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