[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10](S)[CH:11]=2)[CH2:6]1)=[O:4].ClCC1SC(C2C=CC(C(F)(F)F)=CC=2)=NC=1C.[Cl-].C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>C(#N)C.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]
Compound 1C (crude mixture from above, 830 mg) was dissolved in acetonitrile (80 mL) with the chloride 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.50 g, 1.71 mmol) and Cs2CO3 (2.37 g, 7.27 mmol) The reaction mixture was stirred at RT overnight. Ether (50 mL) and H2O were added and stirring was continued for another 5 min. The layers were separated and the aqueous layer was extracted with ether (2×100 mL). The combined organics was dried over MgSO4 and concentrated to an oil. The crude product was purified by column chromatography eluted with EtOAc and hexanes to give the desired product as a thick yellow oil (0.48 g, 28% for 2 steps).
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