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Potassium Carbonate → 2,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one

HRID 406222
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 406222
Br[C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:5]2=[N:6][C:7]=1Cl.B(O)(O)[C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([C:2]2[N:3]=[C:4]3[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:5]3=[N:6][C:7]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 866818522-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one2×

Produkt 1

HCID 666655132,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirrred suspension of 2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one (Intermediate J) (10 g, 38.1 mmol), p-tolylboronic acid (11.39 g, 84 mmol) in MeCN (400 ml) and water (100 ml) under N2 supply, was added solid K2CO3 (fine mesh) (7.90 g, 57.1 mmol) followed by Pd(PPh3)2Cl2 (1.337 g, 1.905 mmol). The yellow RM was heated to 80° C. and was left stirring for 66 hours. The RM was allowed to cool slowly to RT and then placed in the fridge for 3-4 hours. The fine yellow needles were filtered off under suction and were washed with small quantity of acetonitrile, followed by water. After air drying for 10 min, the solid was transferred, dried in vacuo at 40° C. for 2 hours, to afford the title compound as fine crystalline needles;

Aufarbeitung

  1. waitwas left
  2. temperatureto cool slowly to RT
  3. waitplaced in the fridge for 3-4 hours
  4. filtrationThe fine yellow needles were filtered off under suction
  5. washwere washed with small quantity of acetonitrile
  6. customAfter air drying for 10 min
  7. customdried in vacuo at 40° C. for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-d37fa80646be4bd0a39252b6dc636bfa
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754085B2

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