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Sodium Carbonate → 2-[(Phenylmethyl)oxy]-5-(1H-pyrazol-4-yl)-N-3-pyridinylbenzamide

HRID 1623837
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1623837
Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][N:36](C(OC(C)(C)C)=O)[CH:37]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>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>[C:19]1([CH2:18][O:17][C:5]2[CH:4]=[CH:3][C:2]([C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)=[CH:16][C:6]=2[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

Produkt 1

HCID 671080462-[(Phenylmethyl)oxy]-5-(1H-pyrazol-4-yl)-N-3-pyridinylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a microwave vial was added 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 310 mg, 0.81 mmol), 1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (262 mg, 0.89 mmol), 1,4-dioxane (3 ml), sodium carbonate (1.62 ml, 1.62 mmol) and tetrakis(triphenylphosphine)palladium(0) (56.1 mg, 0.05 mmol). The vial was sealed and heated to 120° C. for 25 min under microwave conditions. The mixture was evaporated under reduced pressure and water (5 ml) was added to the residue. The mixture was extracted with ethyl acetate (3×10 ml). The organics were combined and evaporated under reduced pressure, and the residue was purified using the MDAP to yield the title compound. 44 mg.

Aufarbeitung

  1. customThe vial was sealed
  2. customThe mixture was evaporated under reduced pressure and water (5 ml)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
  5. customevaporated under reduced pressure
  6. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-4a2b9882de1c4a57881199719b749b31
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778939B2

Notizen zur Reaktion

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