Sodium Carbonate → HCID 10433189, compound

HRID 966073Notes

Reaction equation

HRID 966073 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.[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[Cl:26][C:27]1[CH:32]=[C:31]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:15]([NH:14][C@H:5]2[CH2:4][O:3][C:2]([CH3:25])([CH3:1])[O:7][C@H:6]2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:16])[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 11744563HCID 11744563, compound

Product 1

HCID 10433189HCID 10433189, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
80 °C

Procedure

To a reaction flask charged with 16.2 mg (0.014 mmol) of Tetrakis(triphenylphosphine)palladium(0) in ethylene glycol dimethyl ether (2.0 mL) under nitrogen was added 142 mg (0.31 mmol) of the product from Example 6 and ethylene glycol dimethyl ether (0.8 mL). The resulting yellow solution was stirred for 10 min before the addition of 57.8 mg (0.37 mmol) of 3-chlorophenylboronic acid dissolved in ethylene glycol dimethyl ether (0.6 mL) and the subsequent addition of 0.32 mL (0.65 mmol) of a 2 M sodium carbonate aqueous solution. The reaction mixture was heated at 80° C. for ˜24 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 was purified by column chromatography (hexane/ethyl acetate) to yield 80 mg (59%) 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 was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c9d1694033024f408762e10faafa4340
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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