Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.FC(F)(F)S(O[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=1)(=O)=O.[F-].[K+].C(Cl)Cl>CN(C=O)C>[NH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=3)=[CH:11][C:6]=2[N:7]=15-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).
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