C(N(S(F)(F)[F:7])CC)C.[Cl:10][C:11]1[C:16]([C:17]2(O)[CH2:20][CH2:19][CH2:18]2)=[CH:15][CH:14]=[C:13]([CH3:22])[N:12]=1>ClCCl>[Cl:10][C:11]1[C:16]([C:17]2([F:7])[CH2:20][CH2:19][CH2:18]2)=[CH:15][CH:14]=[C:13]([CH3:22])[N:12]=1Diethylaminosulfur trifluoride (1.22 g, 1.00 mL, 7.57 mmol) was added to an ice cold solution of 1-(2-chloro-6-methylpyridin-3-yl)cyclobutanol (Example 130 a, 1 g, 5.06 mmol) in dichloromethane (10 mL) keeping the temperature below 5° C. The reaction mixture was stirred for 30 min. at 0° C., poured onto ice water/sat. aqueous Na2CO3 solution (35 mL) and extracted with dichloromethane (2×50 mL). The organic layers were combined, washed with ice water/brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 50 g, heptane/EtOAc 0-10% in 75 min) to give the title compound (939 mg, 93%) as colorless oil, MS (ESI): m/e=200.3 [MH+].
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