Phenylboronic Acid → Oxalate

HRID 572825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572825
I[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:35]([O-:40])(=[O:39])[C:36]([O-:38])=[O:37]>CC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:3]=1.[C:35]([O-:40])(=[O:39])[C:36]([O-:38])=[O:37]

Komponenten

8

Edukt 3

HCID 66827Phenylboronic AcidHCID 71081OxalateHCID 569474582-[(3-Iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole

Produkt 2

HCID 71081OxalateHCID 668359972-[Biphenyl-3-yl(1-methylpiperidin-4-yloxy)methyl]benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 152416121,1`-Bis(diphenylphosphino)ferroceneKatalysatorHCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 2-[(3-iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (200 mg), phenylboronic acid (70 mg), palladium acetate (4.8 mg) and 1,1-bis(diphenylphosphino)ferrocene is placed in a round-bottom flask and purged with argon. A 1M aqueous degassed solution of potassium carbonate (1.51 mL) and degassed tetrahydrofuran (2 mL) are introduced. The mixture is heated at 95° C. for 30 min, cooled back to room temperature and filtered over a celite pad. The cake is rinsed with ethyl acetate and water. The pooled phases are decanted. The organic phase is dried over magnesium sulfate and concentrated. The residue is purified by column chromatography (gradient dichloromethane/methanol from 98/2 to 90/10) to give the crude base which is then converted to the oxalate in acetone to give 2-[biphenyl-3-yl(1-methylpiperidin-4-yloxy)methyl]benzothiazole, oxalate as a beige amorphous solid.

Aufarbeitung

  1. customis placed in a round-bottom flask
  2. custompurged with argon
  3. customA 1M aqueous degassed solution of potassium carbonate (1.51 mL) and degassed tetrahydrofuran (2 mL)
  4. additionare introduced
  5. temperaturecooled back to room temperature
  6. filtrationfiltered over a celite pad
  7. washThe cake is rinsed with ethyl acetate and water
  8. customThe pooled phases are decanted
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue is purified by column chromatography (gradient dichloromethane/methanol from 98/2 to 90/10)
  12. customto give the crude base which

Quellen und Nachweise

ORD-Eintrag
ord-e5341bf0124d43ddaaa765fcaf8ac944
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029357B2

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