Potassium Carbonate → HCID 59643238, compound

HRID 2251539Notes

Reaction equation

HRID 2251539 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][N:32]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][N:32]=2)[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)=[CH:12][CH:11]=1)([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 59643115HCID 59643115, compound

Product 1

HCID 59643238HCID 59643238, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (250 mg; 0.61 mmol), 2-chloro-5-nitro-pyridine (116 mg; 0.73 mmol) and K2CO3 (126 mg; 0.92 mmol) in 2 ml of dioxane was heated at 220C in a pressure tube under nitrogen for 16 hr. Upon cooling, the mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using ethyl acetate-hexane mixtures (2–30% gradient) afforded the title compound (254 mg; 78% yield).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe aqueous phase was washed with ethyl acetate
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by radial chromatography

Sources & evidence

ORD record
ord-89e07f800706492da910ada71f48b0de
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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