C([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:6][CH:5]=1)C.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH:28]([F:30])[F:29]>CN(C=O)C.C(OCC)(=O)C>[F:29][CH:28]([F:30])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:8][CH:9]=1A solution of Step 1 intermediate, Intermediate 10 (400 mg, 1.548 mmol) in DMF (15 ml) was treated with Cs2CO3 (1.513 g, 4.645 mmol) slowly at room temperature. The reaction temperature was raised to 80° C. at which the chloro-difluoro-methane (ClCHF2) gas was passed into the reaction mixture till TLC indicated completion of the reaction. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4 and purified using column chromatography to afford the desired compound; 1H NMR (300 MHz, CDCl3) δ 2.20 (s, 3H), 7.18-7.22 (m, 2H), 7.25 (s, 1H), 7.37-7.40 (m, 2H), 7.55 (d, J=5.1 Hz, 1H), 7.99 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 309.45 (M+H)+.
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