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

HRID 1623835
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1623835
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].[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.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.COCCOC>[CH3:25][N:26]1[CH:30]=[C:29]([C:4]2[C:5]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:6]([CH:16]=[CH:2][CH:3]=2)[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])[CH:28]=[N:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

Produkt 1

HCID 866682161-Methyl-1H-pyrazol-4-yl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

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; 100 mg, 0.26 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (59.7 mg, 0.29 mmol), 1,2-dimethoxyethane (2 ml), 1M sodium carbonate (0.52 ml, 0.52 mmol) and tetrakis(triphenylphosphine)palladium(0) (18.09 mg, 0.02 mmol). The vial was sealed and heated to 120° C. for 25 min under microwave conditions. The mixture was evaporated under reduced pressure. Water (5 ml) was added to the residue and the mixture was extracted with ethyl acetate (3×10 ml). The organics were combined and evaporated and the residue was purified using MDAP to yield the title compound. 31 mg.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2d2f5d0105db475194c5397eb574d580
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778939B2

Notizen zur Reaktion

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