Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:11]3[CH2:16][CH2:15][C:14]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[O:13][C:12]3=[O:27])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][N:31]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([N:11]4[CH2:16][CH2:15][C:14]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[O:13][C:12]4=[O:27])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:33]=[CH:32][N:31]=13-(1-(4-bromophenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (33 mg, 0.078 mmol), 2-methoxypyridine-4-boronic acid pinacol ester (27 mg, 1.5 equiv), Pd(dppf)Cl2 (6 mg, 10% mol), 2M aq Na2CO3 (1 mL), 1,4-dioxane (2.5 mL) were mixed in a tube for microwave oven. The tube was evacuated and refilled with nitrogen gas (3×) and heated in the microwave oven for 120 min at 130° C. LC-MS found the reaction was complete. The mixture was diluted with EtOAc (10 mL), washed with water (4 mL) and brine (3 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 4-g silica gel column, eluted with a 10˜50% EtOAc in hexanes gradient, to afford 3-(1-(4-(2-methoxypyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (26.5 mg, 75%) as a clear oil.
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