C[CH2:2][N:3]([CH:7]([CH3:9])C)[CH:4](C)C.CNC.BrC[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=C[C:16]=1[F:24].CCOC(C)=O>C1COCC1>[F:24][C:16]1[CH:15]=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:9]=1[CH2:7][N:3]([CH3:2])[CH3:4]
A −20° C. solution of DIEA (771 mg, 5.97 mmol) and dimethylamine (2.0M in THF, 1.94 mL, 3.88 mmol) in THF (5 mL) was treated drop-wise with a solution of 2-(bromomethyl)-1-fluoro-4-nitrobenzene (698 mg 2.98 mmol) in THF (5 mL) and stirred at RT overnight as the cooling bath expired. The mixture was treated with EtOAc, washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 1-(2-fluoro-5-nitrophenyl)-N,N-dimethylmethanamine (494 mg, 84% yield). MS (ESI) m/z: 199.1 [M+H]+.
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