Reaktion #529963

Reaktionsgleichung

K2CO3

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

diethyl 3-pyridyl-borane

→

title compound

Ausbeute 81.0%

Methyl 3-amino-5-(3-pyridyl)thieno[3,2-b]pyridine-2-carboxylate

Ausbeute 81.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Sonstigequenched in sat'd NH4Cl
3. 3
   Sonstigethe solid precipitate collected
4. 4
   Sonstigechromatographed 9:1 hexane/EtOAc

Vorschrift

A solution of the methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate prepared as described in Example 5A (0.252 g), diethyl 3-pyridyl-borane (0.155 g), Pd(dppf)Cl2 (0.082 g) and K2CO3 (420 mg) in degassed DMF (5 mL) was heated to 95° C. for 1.5 h, cooled, quenched in sat'd NH4Cl, the solid precipitate collected and chromatographed 9:1 hexane/EtOAc to give 0.24 g (81%) of the title compound: 1H NMR (300MHz, CDCl3) δ 3.95 (3H, s), 6.30 (2H, br s), 7.45 (1H, dd), 7.86 (1H, d), 8.19 (1H, d), 9:1 hexane/EtOAc to give 0.24 g (81%) of the title compound: 1H NMR (300MHz, CDCl3) δ 3.95 (1H, dd), 9.32 (1H, br d).

Quelle