Potassium Carbonate → HCID 22245117, compound

HRID 1279484Notes

Reaction equation

HRID 1279484 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.Br[C:11]1[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)=[O:14].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:26]2[CH:27]=[CH:28][CH:29]=[CH:11][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[CH:17]=2)=[O:14])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 832754-PyridineethanamineHCID 7716632-bromo-N-[3-(trifluoromethyl)phenyl]benzamide2×

Product 1

HCID 22245117HCID 22245117, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

4-Pyridineethanamine (Maybridge Chemical Co, Cornwall, England; 0.31 g , 2.5 mmol) is added to a stirred mixture of 2-bromo-N-[3-(trifluoromethyl)phenyl]benzamide (intermediate 1x; 1.72 g, 5 mmol), powdered potassium carbonate (0.35 g, 2.5 mmol) and copper(1)iodide (Fluka, Buchs, Switzerland; 0.48 g, 2.5 mmol) in dimethylformamide (10 mL). The resulting mixture is then purged with argon and subsequently heated at 160° C. under an argon atmosphere for 15 hours. The mixture is cooled, treated with water (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extracts are washesdwith an aqueous solution of ammonia (2-10%), 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 50% ethyl acetate in hexane and recrystallised from ethyl acetate-hexane to give the title compound as a colourless crystalline solid, m.p. 151-152° 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. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product which
  9. customis purified by column chromatography on silica gel, eluent 50% ethyl acetate in hexane
  10. customrecrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8cd29bcc23894144ac54ba460a2b67f3
Source dataset
uspto-grants-2002_09
Patent number
US06448277B2

Reaction notes

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