Reaktion #529961

Reaktionsgleichung

Methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate

DMF

phenylboronic acid

triethylamine

→

title compound

Ausbeute 50.0%

Methyl 3-amino-5-phenyl-thieno[3,2-b]pyridine-2-carboxylate

Ausbeute 50.0%

Lösungsmittel

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was then cooled
2. 2
   WaschenThe organic layer was washed with H2O, brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigechromatographed (2:1 CH2Cl2 :hexane)

Vorschrift

Methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate, prepared as described in Example 6A (0.243 g, 1.0 mmol), phenylboronic acid (0.134 g, 1.1 mmol) and triethylamine (0.20 mL) were added to 3 mL of DMF containing [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride (1:1 complex with CH2Cl2) under N2. The mixture was stirred at 90° C. for 4 h. The reaction was then cooled and diluted with Et2O. The organic layer was washed with H2O, brine, dried (MgSO4), concentrated and chromatographed (2:1 CH2Cl2 :hexane) to yield the title compound (140 mg, 50%): 1H NMR (300 MHz, CDCl3) δ 3.93 (s, 3H), 6.30 (bs, 2H), 7.41-7.55 (m, 3H), 7.84 (d, J=8 Hz, 1H), 8.07-8.13 (m, 3H); MS (DCI(NH3)) m/e 285 (M+H)+.

Quelle