Boronic acid, [3-chloro-4-(dimethylamino)phenyl]- → HCID 10598294, compound

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Reaction Steps

Following the general procedure outlined in Synthetic Scheme VI, 2.25 g (6.48 mmol) of 1-bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene (Example 18, Step 2) was reacted with 1.68 g (8.42 mmol) of 3-chloro-4-(N,N-dimethylamino)phenylboronic acid (Step 2). Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7) gave 2.65 g (97%) of 2-chloro-4-[4,5-difluoro-2-[4-(methylsulfonyl)phenyl]phenyl]-N,N-dimethylbenzenamine as a colorless solid: mp 129.0°-130.0° C.; NMR (CDCl3) β 2.81 (s, 6H), 3.05 (s, 3H), 6.76-6.91 (m, 2H), 7.08(d, J=2 Hz, 1H), 7.17-7.26 (m, 2H), 7.31 (d, J=8.5 Hz, 2H), 7.83(d, J=8.5 Hz, 2H). MS (FAB): m/e 428 (M+Li). Anal. Calc'd for C21H18 ClF2NO2S: C, 59.79; H, 4.30; N, 3.32. Found: C, 59.40; H, 4.29; N, 3.24.

Provenance & Evidence