Triethylamine → HCID 86621972, compound

HRID 2422508Notes

Reaction equation

HRID 2422508 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:12][C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1)(=O)=O.C(N(CC)CC)C.[C]=O>CS(C)=O>[O:17]=[C:13]1[CH:12]=[C:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:10]2[C:15](=[CH:16][C:7]([C:13]([O:14][CH3:15])=[O:17])=[CH:8][CH:9]=2)[O:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59774869HCID 59774869, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86621972HCID 86621972, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 2-oxo-4-pyridin-3-yl-2H-chromen-7-yl trifluoromethanesulfonate (6.4 g, 17.24 mmol) in DMSO (100 mL) stirred at room temperature, triethylamine (4.85 mL, 34.5 mmol) was added. The reaction was then purged twice with carbon monoxide and palladium dichloride-(dppf)-dichloromethane (2.82 g, 3.45 mmol) was added. The mixture was purged once again with carbon monoxide and the reaction was stirred overnight at 65° C. under carbon monoxide atmosphere. After cooling, the reaction was quenched by the addition of an aqueous saturated ammonium chloride solution. The aqueous layer was extracted (3×) with ethyl acetate and the combined organic extracts were dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/CH2Cl2, 10:90). MS (+ESI) 282.2 (M+H)+.

Workup

  1. additionwas added
  2. customThe mixture was purged once again with carbon monoxide
  3. stirringthe reaction was stirred overnight at 65° C. under carbon monoxide atmosphere
  4. temperatureAfter cooling
  5. customthe reaction was quenched by the addition of an aqueous saturated ammonium chloride solution
  6. extractionThe aqueous layer was extracted (3×) with ethyl acetate
  7. dry with materialthe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-22e9f1382fe746f4b67dbfbf14331725
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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