Reaktion #45409

Reaktionsgleichung

mixture

tert-butyl 4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)phenylcarbamate

4-pyridylboronic acid

Na2CO3

→

desired product

Ausbeute 46.5%

tert-butyl 4-[4-amino-7-(4-pyridinyl)thieno[3,2-c]pyridin-3-yl]phenylcarbamate

Ausbeute 46.5%

Lösungsmittel

THF methanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby bubbling nitrogen through the solution for 15 minutes
2. 2
   SonstigeThe reaction vessel was sealed
3. 3
   TemperaturThe reaction was cooled to room temperature
4. 4
   Sonstigepartitioned between water and ethyl acetate
5. 5
   ExtraktionThe aqueous phase was extracted twice with ethyl acetate
6. 6
   TrocknenThe combined extracts were dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigethe residue was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane

Vorschrift

A mixture of Example 77A (1.559 g, 3.34 mmol), 4-pyridylboronic acid (0.431 g, 3.51 mmol) and Na2CO3 (0.37 g, 3.51 mmol) in THF/methanol/water (12 mL:2.4 mL:4 mL) was degassed by bubbling nitrogen through the solution for 15 minutes, then treated with Pd(dppf)Cl2 (136mg, 0.17 mmol). The reaction vessel was sealed and heated to 90° C. for 17 hours. The reaction was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate. The combined extracts were dried (Na2SO4), filtered, concentrated, and the residue was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane to provide 0.65 g (46%) of the desired product. MS (ESI(+)) m/e 419 (M+H)+.

Quelle