[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]=[O:13])[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[Mg]Br.OS(O)(=O)=O>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([OH:13])[C:24]1[S:23][CH:27]=[CH:26][CH:25]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2The title product from Example 170 Step 1 (100 mg, 0.31 mmol) was dissolved in 1.0 mL of Et2O and cooled to −30° C. To this solution was added 0.31 mL thiophene-2-yl magnesium bromide solution (1.0 M in THF). After 10 minutes, the reaction mixture was pipetted over ice and diluted with ether and a dilute solution of H2SO4. The organic extracts were washed with a saturated solution of NaHCO3, dried over MgSO4, filtered, and evaporated under reduced pressure to dryness to provide 112 mg of a yellow oil. This oil was used as is without further purification.
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