C(OC(NOS(C1C(C)=CC(C)=CC=1C)(=O)=O)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[N:44]O)[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]3[N:44]=2)=[CH:32][CH:31]=1Solid t-butoxycarbonyl-O-mesitylenesulfonylhydroxylamine (17.26 54.6 mmol) was added portionwise with stirring to TFA (50 ml) over 10 min then stirred for a further 30 minutes. The solution was poured onto ice (˜250 ml) and left until the ice melted. The resulting white solid was filtered off, washed with water, and dissolved in chloroform (200 ml). The solution was dried over 4 Å mol. sieves for 1.5 hours, filtered and 1-(4-fluorophenyl)-2-pyridin-2-ylethanone oxime (6.29 g 27.3 mmol) in chloroform (100 ml) was added. The reaction was stirred at room temperature for 18 hours, washed with water (2×50 ml) and dried. Removal of solvent gave a brown solid which was purified by biotage chromatography. Elution with cyclohexane/ethyl acetate (20/1) gave the title compound as a yellow solid (4.09 g 71%). MH+: 213; NMR: (CDCl3): δ 6.75 (2H, m) 7.10 (3H, m) 7.50 (1H, d) 7.95 (2H, m) 8.45 (1H, d).
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