3,6-Dichloropyridazine → 3-Chloro-6-(4-methoxyphenyl)pyridazine

HRID 1993359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993359
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1>C([O-])([O-])=O.[Na+].[Na+].CCO.C1(C)C=CC=CC=1.CCOC(C)=O.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>[Cl:12][C:13]1[N:14]=[N:15][C:16]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][CH:18]=1

Komponenten

7

Edukt 2

HCID 673313,6-DichloropyridazineHCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 122575013-Chloro-6-(4-methoxyphenyl)pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 18778779HCID 18778779, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-methoxyphenylboronic acid (3 g, 0.02 mol) and 3,6-dichloro-pyridazine (3.58 g, 0.024 mol) in 2 M Na2CO3/EtOH toluene (40 mL/20 mL/100 mL) was bubbled through N2 for 5 min. Pd(PPh3)4 (1.15 g, 0.001 mol) was added under N2 and the reaction was heated to 80° C. for 16 h. The mixture was diluted with 100 mL of EtOAc and 20 mL of water. The organic phase was separated, washed with 50 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid obtained was washed with 50% EtOAc/hexane to provide the title compound as off-white solid. MS (ESI pos. ion) m/z: 221.0 (M+H). Calc'd Exact Mass for C11H9ClN2O: 220.65.

Aufarbeitung

  1. customwas bubbled through N2 for 5 min
  2. customThe organic phase was separated
  3. washwashed with 50 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe solid obtained
  7. washwas washed with 50% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-067a44854a4a4735a32477cf98651e46
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652009B2

Notizen zur Reaktion

Wird geladen…