Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH2:13][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:16][CH:17]=1)=[O:11].CCN(CC)CC>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:8][C:6]1[CH:7]=[C:2]2[C:12]3([CH2:17][CH:16]=[CH:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)[C:10](=[O:11])[NH:9][C:3]2=[CH:4][CH:5]=1
To a stirred solution of tert-butyl 3-(2-bromo-4-fluorophenylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate (1.30 g, 3.56 mmol) in DMF (18 mL) under N2 was added successively Et3N (1.13 mL, 8.14 mmol), tetrabutylammonium bromide (1.26 g, 3.91 mmol) and Pd(OAc)2 (0.146 g, 0.651 mmol). The resulting mixture was heated at about 100° C. for 3 h. After cooling, the reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with 1N HCl and brine, dried and concentrated. The residue was purified by column chromatography (hexanes:EtOAc, 4:1) to give tert-butyl 5-fluoro-2-oxo-2′,4′-dihydro-1′H-spiro[indoline-3,3′-pyridine]-1′-carboxylate (0.80 g, 77%). LCMS (APCI+) m/z 219 [M+H-Boc]+; Rt=3.41 min.
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