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Sodium Carbonate → 2-benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-one

HRID 2224236
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2224236
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([O:15][CH3:16])=[C:11](Cl)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.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>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([O:15][CH3:16])=[C:11]([C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 135262132-Benzyl-5-chloro-4-methoxypyridazin-3(2H)-one

Produkt 1

HCID 569275222-benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-oneAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one (20.0 g, 79.8 mmol) in toluene (500 mL) was added Pd(PPh3)4 (5.5 g, 4.76 mmol) under an atmosphere of argon. 4-Chlorophenylboronic acid (18.7 g, 119.6 mmol) was added subsequently. Under vigorous stirring, Na2CO3 (33.8 g, 318.9 mmol) pre-dissolved in water (90 mL) was added to the suspension. A stream of argon was bubbled through this suspension for 10 min. After this time, the flask was placed in an oil bath preheated at 120° C. The reaction was refluxed for 3 h. After this time, the reaction was cooled to RT The reaction mixture was then poured into water (200 mL). The layers were separated and the aqueous mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water (2×200 mL) followed by saturated aqueous NaCl (2×100 mL). The organic layer was then concentrated under reduced pressure to obtain crude product. This crude product was purified by silica gel column chromatography eluting with 8% EtOAc/hexanes to give the title compound, 2-benzyl-5-(4-chlorophenyl)-4-methoxypyridazin-3(2H)-one, (21.5 g, 82%) as a white solid. HPLC: 3.79 min; M+H=327. 1H NMR (CDCl3, 500 MHz): δ 7.76 (1H, s), 7.48 (2H, d, J=10.0 Hz), 7.40-7.45 (4H, m), 7.28-7.36 (3H, m), 5.35 (2H, s), 4.10 (3H, s).

Aufarbeitung

  1. additionwas added to the suspension
  2. customA stream of argon was bubbled through this suspension for 10 min
  3. customAfter this time, the flask was placed in an oil bath
  4. custompreheated at 120° C
  5. temperatureThe reaction was refluxed for 3 h
  6. additionwas then poured into water (200 mL)
  7. customThe layers were separated
  8. extractionthe aqueous mixture was extracted with EtOAc (100 mL×3)
  9. washThe combined organic layers were washed with water (2×200 mL)
  10. concentrationThe organic layer was then concentrated under reduced pressure
  11. customto obtain crude product
  12. customThis crude product was purified by silica gel column chromatography
  13. washeluting with 8% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b28a5a7d29a24a5fb7b7549695aa307a
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07378418B2

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