CO[C:3]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12]C2)C=CC=1N.F[C:16]1[CH:17]=[CH:18][C:19]([N+:26]([O-])=O)=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.CC1CCCNC1.CC#N>O>[CH3:12][CH:13]1[CH2:3][CH2:9][CH2:8][N:10]([C:16]2[CH:17]=[CH:18][C:19]([NH2:26])=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=2)[CH2:14]12-Methoxy-4-(pyrrolidin-1-yl)aniline can be synthesized following the general scheme above starting from 5-fluoro-2-nitrobenzotrifluoride and 3-methylpiperidine. 1H NMR (400 MHz, CDCl3) δ 7.05-6.93 (m, 2H), 6.69 (d, J=8.7 Hz, 1H), 3.85 (s, 2H), 3.42-3.29 (m, 2H), 2.52 (td, J=11.5, 3.1 Hz, 1H), 2.25-2.15 (m, 1H), 1.86-1.62 (m, 5H), 0.94 (d, J=6.4 Hz, 3H). LC/MS: m/z 259.0 (M+H)+ at 0.79 min (10%99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
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