ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[C:18]([C:19]2([F:23])[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=[C:15]([CH3:24])[N:14]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[Cl:12][C:13]1[C:18]([C:19]2([F:23])[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=[C:15]([CH3:24])[N+:14]=1[O-:6]3-Chlorobenzoperoxoic acid (173 mg, 1.00 mmol) was added in 2 portions to a solution of 2-chloro-3-(1-fluorocyclobutyl)-6-methylpyridine (Example 130 b, 100 mg, 501 μmol) in dichloromethane (2 mL). The reaction mixture was stirred at ambient temperature for 72 h, poured onto a 10% aqueous Na2S2O3 solution (30 mL) and extracted with dichloromethane (2×40 mL). The combined organic layers were washed with ice water/brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with sat. NaHCO3 solution (30 mL) and ice water (30 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (81 mg, 74%) as yellow oil, MS (ESI): m/e=216.3 [MH+].
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