Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[F:20].[CH3:21][Zn]C.CO.Cl>O1CCOCC1.C(OCC)(=O)C>[CH:11]1([N:8]2[C:9]3[C:5](=[CH:4][C:3]([F:20])=[C:2]([CH3:21])[CH:10]=3)[C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7]2)[CH2:15][CH2:14][CH2:13][CH2:12]1A mixture of methyl 6-bromo-1-cyclopentyl-5-fluoro-1H-indole-3-carboxylate (3.4 g, 10 mmol), dimethylzinc (1.2 M, 16.7 mL, 20 mmol) and PdCl2dppf (163 mg, 0.2 mmol) in dioxane (20 mL) was stirred at 88° C. for 2 hr under nitrogen atmosphere. The mixture was then cooled and methanol was added in slowly followed by 2 N HCl. The mixture was treated with ethyl acetate, washed with water and brine, dried and evaporated. The residue was purified by flash chromatography with dichloromethane and hexane (1:1) to give methyl 1-cyclopentyl-5-fluoro-6-methyl-1H-indole-3-carboxylate (2.66 g, yield 97%).
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