Reaktion #330752

Reaktionsgleichung

5-chlorothieno[3,2-b]pyridine-6-carbaldehyde

phenylboronic acid

K2CO3

→

title compound

Ausbeute 86.5%

5-Phenylthieno[3,2-b]pyridine-6-carbaldehyde

Ausbeute 86.5%

Lösungsmittel

DME water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   Temperaturto cool to room temperature
3. 3
   workup.ADDITIONdiluted with EtOAc (25 mL)
4. 4
   Waschenwashed with water (2×10 mL)
5. 5
   Waschenwashed with brine (10 mL)
6. 6
   SonstigeThe organic layer was separated
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Sonstigethe solvent removed in vacuo
10. 10
    SonstigeThe residue was purified by column chromatography (SiO2, 0-40% EtOAc in heptane)

Vorschrift

To a solution of 5-chlorothieno[3,2-b]pyridine-6-carbaldehyde (396 mg, 2.01 mmol) in DME/water (10 mL/2 mL) was added phenylboronic acid (306 mg, 2.51 mmol), K2CO3 (833 mg, 6.03 mmol) and Pd(PPh3)4 (116 mg, 0.1 mmol). The mixture was degassed before being heated in a sealed tube at 100° C. for 5 h. The reaction mixture was allowed to cool to room temperature, diluted with EtOAc (25 mL), washed with water (2×10 mL) and washed with brine (10 mL). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, 0-40% EtOAc in heptane) to give the title compound (416 mg, 86%) as a white solid. δH (CDCl3) 10.15 (s, 1H), 8.88 (s, 1H), 8.97 (d, J 6 Hz, 1H), 7.69 (d, J 6 Hz, 1H), 7.50-7.65 (m, 5H). LCMS (ES+) 240.2 (M+H)+, RT 3.46 minutes (Method 2).

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