Br[C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[S:5][CH:6]=1.[Li]CCCC.[F:18][C:19]([F:27])([F:26])[C:20](N(OC)C)=[O:21]>C(OCC)C.C1COCC1>[F:18][C:19]([F:27])([F:26])[C:20]([C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[S:5][CH:6]=1)=[O:21]To a chilled (−78° C.) solution of 4-(4-bromothiazol-2-yl)morpholine (249 mg, 1.00 mmol) in dry diethyl ether (10 mL) was added n-BuLi (480 μL, 2.5 M in hexanes, 1.20 mmol). After 20 minutes, a solution of 2,2,2-trifluoro-N-methoxy-N-methylacetamide (224 μL, 2 mmol) in THF (10 mL) was added over 10 minutes. After 30 minutes, the mixture was warmed to 0° C. After 30 minutes, the mixture was quenched with 10 mL of water, warmed to room temperature, and extracted with three 10 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was twice purified on SiO2 using ethyl acetate-hexanes (20-100% gradient) to afford 125 mg (47%) of the title compound.
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