Reaktion #1344649

Reaktionsgleichung

4-methoxycarbonylphenylboronic acid

sodium carbonate

compound

{4-[2-(benzyloxy)phenyl]-1,3-thiazol-2-yl}methanol

triethylamine

methanesulfonylchloride

sodium iodide

→

title compound

Ausbeute 21.7%

methyl-4-({4-[2-(benzyloxy)phenyl]-1,3-thiazol-2-yl}methyl)benzoate

Ausbeute 21.7%

Lösungsmittel

1,2-dimethoxyethane ethanol

tetrahydrofuran

Water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe resulting salt was filtered
2. 2
   Sonstigeremoved
3. 3
   Sonstigethe solvent was evaporated under reduced pressure
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature overnight
5. 5
   Extraktionthe mixture was extracted with ethyl acetate
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   workup.STIRRINGthe mixture was stirred at 90° C. overnight
8. 8
   FiltrationThe resulting salt was filtered
9. 9
   Sonstigeremoved
10. 10
    Sonstigethe solvent was evaporated under reduced pressure
11. 11
    SonstigeThe obtained crude product
12. 12
    Sonstigewas purified by column chromatography (hexane-hexane/ethyl acetate=85/15)

Vorschrift

To a solution (8 mL) of the compound (1.2 g, 4.0 mmol) obtained in Example 191a in tetrahydrofuran were added triethylamine (0.73 mL, 5.3 mmol) and methanesulfonylchloride (0.38 mL, 4.8 mmol), and the mixture was stirred at room temperature for 3 hr. The resulting salt was filtered and removed, and the solvent was evaporated under reduced pressure. To a solution (40 mL) of the residue in acetone was added sodium iodide (1.8 g, 12 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. To a mixed solution of the residue, 4-methoxycarbonylphenylboronic acid (870 mg, 4.8 mmol) and 2M aqueous sodium carbonate solution (2.4 mL, 4.8 mmol) in 1,2-dimethoxyethane/ethanol (v/v=3/1, 12 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (330 mg, 0.40 mmol), and the mixture was stirred at 90° C. overnight. The resulting salt was filtered and removed, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=85/15) to give the title compound (360 mg, 21% in 3 steps) as colorless crystals.

Quelle