Sodium Carbonate → HCID 44393285, compound

HRID 966077Notes

Reaction equation

HRID 966077 reaction equation
[CH3:1][C:2]1([CH3:25])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2I)=[O:16])[CH2:4][O:3]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1([CH3:25])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[O:16])[CH2:4][O:3]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11744563HCID 11744563, compound

Product 1

HCID 44393285HCID 44393285, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a reaction flask charged with 10.8 mg (0.0094 mmol) of tetrakis(triphenylphosphine)palladium(0) in ethylene glycol dimethyl ether (1.8 mL) under nitrogen was added 107 mg (0.24 mmol) of the product from Example 6. The resulting yellow solution was stirred for 15 min before the addition of 34.0 mg (0.28 mmol) of pyridine-3-boronic acid dissolved in ethanol (0.4 mL) and ethylene glycol dimethyl ether (0.2 mL), and the subsequent addition of 0.23 mL (0.47 mmol) of a 2 M sodium carbonate aqueous solution. The reaction mixture was heated at 80° C. for ˜20 h and then cooled to room temperature. The liquid was separated from the solid residue, and the residue was rinsed with dichloromethane, which was subsequently combined with the isolated liquid. The solvent was evaporated, and the crude product was partitioned between brine (˜4 mL) and dichloromethane (˜4 mL). The organic layer was washed with additional brine, dried over magnesium sulfate, and filtered. The solvent was evaporated, and the residue, an orange oil, was purified by column chromatography (hexane/ethyl acetate) to yield 35 mg (36%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customThe liquid was separated from the solid residue
  3. washthe residue was rinsed with dichloromethane, which
  4. customThe solvent was evaporated
  5. customthe crude product was partitioned between brine (˜4 mL) and dichloromethane (˜4 mL)
  6. washThe organic layer was washed with additional brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated
  10. customthe residue, an orange oil, was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f8d1b962b31a4481803ba2f5dd522aab
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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