Reaktion #797287

Reaktionsgleichung

CH2Cl2

5-Bromobenzo[d]oxazol-2-amine

tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

Potassium fluoride

→

titled compound

Ausbeute 44.7%

Tert-butyl 4-(2-aminobenzo[d]oxazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Ausbeute 44.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture was purged with N2 for 30 mins Pd(dppf)2Cl2
2. 2
   Sonstigeagain purged with N2 for 30 mins
3. 3
   Sonstigefollowed by column purification on combiflash
4. 4
   workup.ADDITIONa gradient mixture of EtOAc and Petether (1:1) as eluent

Vorschrift

5-Bromobenzo[d]oxazol-2-amine (824 mg, 3.9 mmol) and tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (1.8 g, 5.8 mmol), Potassium fluoride (674 mg, 11.61 mmol) were dissolved in DMF under N2 atmosphere. This mixture was purged with N2 for 30 mins Pd(dppf)2Cl2.CH2Cl2 (252 mg, 0.3 mmol) was added to the above mixture and again purged with N2 for 30 mins. The reaction mixture was stirred at 90° C. for 12 h. Work up (EtOAc/H2O) followed by column purification on combiflash using a gradient mixture of EtOAc and Petether (1:1) as eluent afforded the titled compound (550 mg) as an off-white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.38-7.36 (m, 2H), 7.26-7.22 (m, 2H), 7.02 (d, J 7.9, 1H), 6.05 (s, 1H), 4.01-3.90 (m, 2H), 3.49-3.55 (m, 2H), 2.50-2.40 (m, 2H), 1.50 (s, 9H).

Quelle