To zinc (167 mg, 2.55 mmol) in dry THF (500 μl) in a dry flask under an argon atmosphere was added 1,2-dibromoethane (5.49 μl, 63.7 μmol). The mixture was heated three times to reflux with a heat gun and allowed to cool to room temperature. Then chlorotrimethylsilane (0.27 μl, 2.12 μmol) was added and the mixture was stirred at room temperature for 20 min. Subsequently the flask was placed in an ice bath and a solution of 3-fluoro-2-methyl-benzylbromide (259 mg, 1.27 mmol) in dry THF (1 ml) was added slowly so that the temperature remained at 0° C. The mixture was stirred at 0° C. for 4.5 h and placed in the refrigerator overnight. Then the cooled mixture was added dropwise to a precooled solution (−78° C.) of B-OM-9-BBN (2.12 ml, 2.12 mmol, 1 M) in hexane. The mixture was stirred at room temperature for 30 min. DMF (5 ml) was added, followed by the compound of step 6 (100 mg, 212 μmol), palladium(II) acetate (4.77 mg, 21.2 μmol) and S—PHOS (17.4 mg, 42.5 μmol). The reaction mixture was stirred at 100° C. for 3 h. After cooling, the mixture was quenched with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by silica gel chromatography (EA (10 to 60%) HEP) to give 90 mg of the title compound.
