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Potassium Phosphate, Tribasic → Ethyl 2-[1-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrate

HRID 390665
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 390665
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[CH2:20][CH3:21])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:22][N:23]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)[C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.[Cl-].[NH4+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[CH2:20][CH3:21])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=1[C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([N:23]([CH3:22])[C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:25])[CH:33]=1)[CH2:2][CH2:3][CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 672732723-(1-Methyl-3-pentylureido)phenylboronic acidHCID 68957093Ethyl 2-[1-(3-butoxy-4-iodophenyl)meth-(e)-ylidene]butyrate

Produkt 1

HCID 68964170Ethyl 2-[1-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845
palladium(II) acetate
Katalysator
HCID 27342162-(Dicyclohexylphosphino)biphenylKatalysator
HCID 6228DimethylformamideLösungsmittel
HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
92.5 °C

Versuchsvorschrift

3 mg (0.013 mmol) of palladium acetate and then 9 mg (0.026 mmol) of 2-(dicyclohexylphosphino)biphenyl are added to a mixture of 523 mg (1.3 mmol) of ethyl 2-[1-(3-butoxy-4-iodophenyl)meth-(E)-ylidene]butyrate (prepared according to Example 22a), 446 mg (1.7 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid (prepared according to Example 24h) and 1.3 mL of aqueous 2 M potassium phosphate solution in 6.5 mL of dimethylformamide. The reaction mixture is heated at 90-95° C. for 2 hours. The reaction medium is hydrolyzed in saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over magnesium sulfate. After filtration, the solvent is evaporated off and the brown oil obtained (1.2 g) is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 489 mg (76%) of ethyl 2-[1-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate are obtained.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent is evaporated off
  6. customthe brown oil obtained (1.2 g)
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 70/30 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-69ccf208a7874709b0f5164158eb0842
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08383652B2

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