Potassium Carbonate → HCID 9843152, compound

HRID 1168221Notes

Reaction equation

HRID 1168221 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.Cl[C:11]1[C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 832754-PyridineethanamineHCID 683662STK3454632×

Product 1

HCID 9843152HCID 9843152, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Pyridineethanamine (Maybridge Chemical Co, Cornwall, England; 0.31 g, 2.5 mmol) is added to a stirred mixture of 2-chloro-N-[3(trifluoromethyl)phenyl]-3-pyridinecarboxamide (intermediate 1a; 0.90 g, 3 mmol), powdered potassium carbonate (0.35 g, 2.5 mmol) and copper(1)iodide; 0.48 g, 2.5 mmol) in dimethylformamide (10 mL). The resulting mixture is then purged with argon and subsequently heated at 100° C. under an argon atmosphere for 2 hours. The mixture is cooled, treated with water (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extracts are washed with an aqueous solution of ammonia (2×50 mL of 10%), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate and recrystalised from ethyl acetate—hexane to give the title compound as a colourless crystalline solid, m.p. 128-138° C.

Workup

  1. customThe resulting mixture is then purged with argon
  2. temperatureThe mixture is cooled
  3. additiontreated with water (100 mL)
  4. extractionextracted with ethyl acetate (3×80 mL)
  5. washThe combined extracts are washed with an aqueous solution of ammonia (2×50 mL of 10%)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent is evaporated off under reduced pressure
  9. customto yield the crude product which
  10. customis purified by column chromatography on silica gel, eluent ethyl acetate
  11. customrecrystalised from ethyl acetate—hexane

Sources & evidence

ORD record
ord-5cbe809527fc46d6955cf42cd11bbf3c
Source dataset
uspto-grants-2003_09
Patent number
US06624174B2

Reaction notes

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