Reaktion #660007

Reaktionsgleichung

oxalate

2-[(3-iodophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole

phenylboronic acid

→

2-[biphenyl-3-yl(1-methylpiperidin-4-yloxy)methyl]benzothiazole

oxalate

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis placed in a round-bottom flask
2. 2
   Sonstigepurged with argon
3. 3
   SonstigeA 1M aqueous degassed solution of potassium carbonate (1.51 mL) and degassed tetrahydrofuran (2 mL)
4. 4
   workup.ADDITIONare introduced
5. 5
   Temperaturcooled back to room temperature
6. 6
   Filtrationfiltered over a celite pad
7. 7
   WaschenThe cake is rinsed with ethyl acetate and water
8. 8
   SonstigeThe pooled phases are decanted
9. 9
   TrocknenThe organic phase is dried over magnesium sulfate
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue is purified by column chromatography (gradient dichloromethane/methanol from 98/2 to 90/10)
12. 12
    Sonstigeto give the crude base which

Vorschrift

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.

Quelle