[Li]CCCC.[F:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[N:11][CH:12]=1.CN(CCN(C)C)C.[I:28]I>C1COCC1>[F:6][C:7]1[C:8]([I:28])=[C:9]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])[CH:10]=[N:11][CH:12]=1
A 2.5M solution of nBuLi (30.6 mL, 76 mmol) in hexanes was added drop-wise to a solution of N-(5-fluoropyridin-3-yl)-2,2-dimethylpropanamide 5.0 g, 25.5 mmol) and TMEDA (11.54 mL, 76 mmol) in THF (127 mL) at −78° C. over 1 hour, while ensuring the internal temperature did not go above −70° C. The resulting solution was stirred at −78° C. for 1 hour. Iodine (19.40 g, 76 mmol) in THF (20 mL) was added drop-wise over 30 min ensuring the internal temperature remained below −70° C. The resulting reaction was stirred for 1 hour at −78° C. The reaction was quenched at −78° C. with water and then warmed to ambient temperature. 10% Aqueous sodium thiosulfate was added until the iodine color dissipated and the mixture was extracted with ethyl acetate (×3). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to afford the title compound (8.21 g, 25.5 mmol, 100% yield), MS (ESI): m/z=323.26 (MH+), 100% pure by LCMS.
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