Potassium Carbonate → Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

HRID 899894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899894
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([O:26][CH3:25])=[O:36])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 69120491N-(2,4-difluorobenzyl)-3-(4-hydroxyphenyl)-N-propylpropanamide

Produkt 1

HCID 69179959Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-(2,4-Difluorobenzyl)-3-(4-hydroxyphenyl)-N-propylpropanamide (290 mg, 0.87 mmol) was dissolved in acetonitrile (10 ml). 2-Bromomethyl-benzoic acid methyl ester (209 mg, 0.913 mmol) was added followed by potassium carbonate, anhydrous (180 mg, 1.305 mmol). The mixture was heated to reflux overnight and then evaporated to dry. Water and ethyl acetate were added and two phases were separated. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE®SI, 20 g/70 ml) using DCM and then MeOH/DCM (1:99) as eluant gave 184 mg the desired product, yield 44%.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionWater and ethyl acetate were added
  6. customtwo phases were separated
  7. dry with materialThe organic phase was dried (magnesium sulphate)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b117dbd55e164740be3ee074969ee399
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07355069B2

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