1,1'-Carbonyldiimidazole → HCID 59864622, compound

HRID 1497668Notes

Reaction equation

HRID 1497668 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=O.[CH2:8]([K])[CH3:9].[Mg+2].[Cl-].[Cl-].[F:14][C:15]1[C:16](C(O)=O)=[N:17][CH:18]=[CH:19][CH:20]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1.O>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][C:3]([C:16]1[C:15]([F:14])=[CH:20][CH:19]=[CH:18][N:17]=1)=[O:5])[CH3:9]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 27627863-Fluoropyridine-2-carboxylic acidHCID 5360315Magnesium ChlorideHCID 178461627HCID 178461627, compound

Product 1

HCID 59864622HCID 59864622, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl potassium malonate (2) (452 mg, 2.66 mmol) in tetrahydrofuran (5 mL) was added MgCl2 (202 mg, 2.13 mL). The mixture was stirred at 50° C. for 4 h and then cooled to room temperature. In another flask a solution of 3-fluoro-pyridine-2-carboxylic acid (1) (250 mg, 1.77 mmol) in tetrahydrofuran (5 mL) was taken and CDI (carbonyldiimidazole) (489 mg, 3.01 mmol) was added at 10° C. The mixture was stirred at room temperature for 1 h, this reaction mixture was then added to the above suspension and stirred at room temperature for 18 h. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. additionthis reaction mixture was then added to the above suspension
  4. stirringstirred at room temperature for 18 h
  5. additionwas added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0fbbb22fccd4481b8eaf2fb12366883b
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

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