Potassium Carbonate → HCID 12216708, compound

HRID 2071138Notes

Reaction equation

HRID 2071138 reaction equation
I[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].B1([C:30]2[N:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)OCCN(C2C=CC=CC=2)CCO1.C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:35]1[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=1[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2758568Dimethyl 5-iodoisophthalateHCID 161199656-Phenyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane

Product 1

HCID 12216708HCID 12216708, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To dimethyl 5-iodoisophthalate (Matrix Scientific, 800 mg, 2.5 mmol) in THF (20 ml), 2-pyridine boronic acid N-phenyldiethanol amine ester (Aldrich, 1.8 g, 6.6 mmol), K2CO3 (912 mg, 6.6 mmol), triphenyl phosphine (173 mg, 0.66 mmol) were added followed by Pd(OAc)2 and cuprous iodide (251 mg, 1.32 mmol). After refluxing for 24 h, reaction mixture was filtered through a pad of celite. Residual solvent was evaporated on a rotavap under reduced pressure and the crude was dissolved in ethyl acetate. Insoluble material was filtered off and the remaining residue was evaporated to dryness and column purified (60% ethylacetate/40% hexanes) to yield 400 mg of dimethyl 5-(pyridin-2-yl)isophthalate as yellow solid.

Workup

  1. temperatureAfter refluxing for 24 h
  2. customreaction mixture
  3. filtrationwas filtered through a pad of celite
  4. customResidual solvent was evaporated on a rotavap under reduced pressure
  5. dissolutionthe crude was dissolved in ethyl acetate
  6. filtrationInsoluble material was filtered off
  7. customthe remaining residue was evaporated to dryness and column
  8. custompurified (60% ethylacetate/40% hexanes)

Sources & evidence

ORD record
ord-d0f8cf0b2f6c4592bfed023d7a90adfc
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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