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Potassium Phosphate, Tribasic → HCID 86630875, Verbindung

HRID 17553
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17553
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:9][C:10]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([N:21]2[CH2:25][CH2:24][C@H:23]([N:26]([CH3:28])[CH3:27])[CH2:22]2)[C:15](Br)=[C:14]([CH3:30])[C:11]=1[C:12]#[N:13].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[NH2:9][C:10]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([N:21]2[CH2:25][CH2:24][C@H:23]([N:26]([CH3:28])[CH3:27])[CH2:22]2)[C:15]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:14]([CH3:30])[C:11]=1[C:12]#[N:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 866308742-Amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile

Produkt 1

HCID 86630875HCID 86630875, VerbindungAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Potassium phosphate (115 mg, 0.54 mmol) and Pd(PPh3)4 (16 mg, 5 mol %) were added to a dioxane (3 ml) solution of 2-amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile (I-267) (100 mg, 0.27 mmol) and phenylboronic acid (40 mg, 0.33 mmol), followed by purging with nitrogen and heating under reflux for 18 hours. After cooling, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the residue was subjected to column chromatography, and eluted with a mixed solvent of chloroform/methanol (2:1, v/v) to obtain the entitled compound (89 mg, 90%) as a dark red solid.

Aufarbeitung

  1. customby purging with nitrogen
  2. temperatureheating
  3. temperatureunder reflux for 18 hours
  4. temperatureAfter cooling
  5. additionwater was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. washeluted with a mixed solvent of chloroform/methanol (2:1

Quellen und Nachweise

ORD-Eintrag
ord-84f4ddda690b40b8a02f0582e27a5e7a
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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