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

HRID 1839945Notes

Reaction equation

HRID 1839945 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[N:27]([CH3:29])[CH3:28]>>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=2[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:24]=[CH:25][C:26]=1[N:27]([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 10608071Boronic acid, [3-chloro-4-(dimethylamino)phenyl]-HCID 117919231-Bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene

Product 1

HCID 10598294HCID 10598294, compoundYield 97%

Procedure

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) δ 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 C21H18ClF2NO2S: C, 59.79; H, 4.30;N, 3.32. Found: C, 59.40; H, 4.29; N, 3.24.

Workup

  1. customPurification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7)

Sources & evidence

ORD record
ord-e7bd9402d56540ab95e8fa0965fb9cc8
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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