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

HRID 1993363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993363
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=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:13][C:14]1[N:15]=[N:16][C:17]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[CH:18][CH:19]=1

Komponenten

7

Edukt 2

HCID 673313,6-DichloropyridazineHCID 27821943-Fluoro-4-methoxyphenylboronic acid

Produkt 1

HCID 203982843-Chloro-6-(3-fluoro-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 3-fluoro-4-methoxyphenylboronic acid (10 g, 0.059 mol) and 3,6-dichloro-pyridazine (8.79 g, 0.059 mol) in 2 M Na2CO3/EtOH/toluene (80 mL/40 mL/200 mL) was bubbled through N2 for 5 min. Cat. Pd(PPh3)4 (3.47 g, 0.003 mol) was added under N2 and the reaction was heated to 80° C. for 16 h. The mixture was diluted with 200 mL of EtOAc and 40 mL of water. The organic phase was separated, washed with 80 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid obtained was washed with 50% EtOAc/hexane to provide off-white solid. MS (ESI pos. ion) m/z: 239.0 (M+H). Calc'd Exact Mass for C11H8ClFN2O: 238.65.

Aufarbeitung

  1. customwas bubbled through N2 for 5 min
  2. customThe organic phase was separated
  3. washwashed with 80 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe solid obtained
  7. washwas washed with 50% EtOAc/hexane
  8. customto provide off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-8af5266fe87e48ff985cff11eec9634e
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652009B2

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