[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=O)[C:7]2([CH3:13])[CH3:12].COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+].O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][C:7]2([CH3:13])[CH3:12]A mixture of 7-fluoro-3,3-dimethyloxindole (EXAMPLE 99, step 5, 2.24 g 12.5 mmol) in toluene (15 mL) under nitrogen was heated at 80° C. Vitride (65 wt % in toluene, 6 mL, 19.3 mmol) was added dropwise via an addition funnel. The resulting solution was stirred at 80° C. for an additional 1.5 hours, then cooled in an ice bath. Aqueous sodium hydroxide solution (1N, 15 mL) was added slowly to quench the reaction. Water (15 mL) was added and the reaction mixture was extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried (anhydrous sodium sulfate), filtered through a pad of silica gel, and concentrated under reduced pressure to yield 1.68 g (82%) of 7-fluoro-3,3-dimethylindoline as a colorless oil. MS (ES) m/z 166.1 ([M+H]+); HRMS: calcd for C10H12FN+H+, 166.1032; found (ESI, [M+H]+), 166.1040.
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