Potassium Carbonate → HCID 86692450, compound

HRID 1748497Notes

Reaction equation

HRID 1748497 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])C.[I:11][C:12]1[CH:13]=[CH:14][C:15](F)=[N:16][CH:17]=1.CNC1CCCCC1NC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O>[I:11][C:12]1[CH:13]=[CH:14][C:15]([N:9]2[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]2)=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 27831792-Fluoro-5-iodopyridine

Product 1

HCID 86692450HCID 86692450, compoundYield 8.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1H-pyrazole-4-carboxylic acid ethyl ester (2.00 g), 5-iodo-2-fluoropyridine (1.68 g), copper (I) iodide (136 mg), N,N′-dimethyl-1,2-cyclohexanediamine (5 ml) and potassium carbonate (4.06 g) was stirred at 120° C. for 48 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was dissolved in ethanol (10 ml), sodium hydroxide (568 mg) was added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated by an evaporator, the aqueous solution was acidified by the addition of 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the titled compound (207 mg) as a dark brown solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethanol (10 ml)
  6. additionsodium hydroxide (568 mg) was added
  7. stirringthe mixture was stirred at room temperature overnight
  8. concentrationThe reaction solution was concentrated by an evaporator
  9. additionthe aqueous solution was acidified by the addition of 1N hydrochloric acid aqueous solution
  10. extractionextracted with ethyl acetate
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-f03ebe6f571f4f3aae915b7d45c2eecc
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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