Sodium Carbonate → HCID 9978820, compound

HRID 966072Notes

Reaction equation

HRID 966072 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.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1B(O)O.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:27]2[S:26][CH:30]=[CH:29][CH:28]=2)=[O:16])[CH2:4][O:3]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 11744563HCID 11744563, compound

Product 1

HCID 9978820HCID 9978820, compoundYield 37.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

To a reaction flask charged with 10.6 mg (0.0092 mmol) of tetrakis(triphenylphosphine)palladium(0) in ethylene glycol dimethyl ether (1.8 mL) under nitrogen was added 104 mg (0.23 mmol) of the product from Example 6. The resulting yellow solution was stirred for 10-15 min before the addition of 34.5 mg (0.27 mmol) of 2-thiopheneboronic acid dissolved in ethanol (0.2 mL) and ethylene glycol dimethyl ether (0.2 mL) and the subsequent addition of 0.23 mL (0.46 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 dark residue was purified by column chromatography (hexanes/ethyl acetate) to yield 35 mg (37%) 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 dark residue was purified by column chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-dff2c8ae3e9241cc86d2b90b6bb9eaa8
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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