Br[C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].Cl.CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:21][C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11]Following general method A-18, 7-Bromo-5-fluoro-3-methyl-1H-indole (727 mg, 3.19 mmol) was reacted with 3,4-dichlorophenol (779 mg, 4.78 mmol), CuI (60.8 mg, 0.319 mmol), N,N-dimethylglycine hydrochloride (134 mg, 0.957 mmol), and Cs2CO3 (2.07 g, 6.38 mmol) in anhydrous dioxane (6.4 mL). The crude product was purified by silica gel column chromatography utilizing a solvent system of 5% EtOAc/Hexanes to yield 506 mg of I-198C as a yellow oil (34%). 1H NMR (400 MHz, CDCl3).
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