Réaction #46242

Équation de réaction

4-cyanobenzeneboronic acid

(6-bromo-pyridin-2-yl)carbamic acid tert-butyl ester

K2CO3

→

[6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester

Rendement 60.0%

Solvants

DMF H2O

Conditions de réaction

Traitement

1. 1
   AutreDMF was evaporated off under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (200 mL)
3. 3
   LavageThe mixture was washed with water and brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated to dryness
6. 6
   AutreThe residue was purified by column (Petroleum Ether/EtOAc 50:1) on silica gel

Mode opératoire

A mixture of 4-cyanobenzeneboronic acid (7.35 g, 50 mmol), (6-bromo-pyridin-2-yl)carbamic acid tert-butyl ester (13.8 g, 50 mmol), Pd(Ph3P)4 (5.8 g, 0.15 mmol) and K2CO3 (10.4 g, 75 mmol) in DMF/H2O (1:1, 250 mL) was stirred under argon at 80° C. overnight. DMF was evaporated off under reduced pressure and the residue was dissolved in EtOAc (200 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by column (Petroleum Ether/EtOAc 50:1) on silica gel to give [6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester (7.0 g, 60%). 1H NMR (300 MHz, CDCl3) δ 8.02-8.07 (m, 2H), 7.95 (d, J=8.4 Hz, 1H), 7.71-7.79 (m, 3H), 7.37-7.44 (m, 2H), 1.53 (s, 9H).

Source