3,4-Dimethoxyphenylboronic acid → HCID 10668927, compound

HRID 1839952Notes

Reaction equation

HRID 1839952 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.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>>[F:9][C:5]1[CH:4]=[C:3]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[C:2]([C:25]2[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[C:27]([O:28][CH3:29])[CH:26]=2)=[CH:7][C:6]=1[F:8]

Participants

3

Reactant 2

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 117919231-Bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene

Product 1

HCID 10668927HCID 10668927, compound

Procedure

Following the general procedure outlined in Synthetic Scheme VI, 1-bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene (Example 18, Step 2) was reacted with 3,4-dimethoxyphenyboronic acid (step 1) to give 1,2-difluoro-4-(3,4-dimethoxypheny)-5-[4(methylsulfonyl)phenyl]benzene as a colorless solid: mp 140.0-141.0° C.; NMR (CDCl3) δ 3.04 (s, 3H), 3.61 (s, 3H), 3.86 (S, 3H), 6.48 (d, J=2 Hz, 1H), 6.65 (dd, J=2, 8 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 7.17-7.29 (m, 2H), 7.31 (d, J=8 Hz, 2H), 7.81 (d, J=8 Hz, 2H); MS (FAB) m/z 411 (M+Li)+; HRMS calc'd for M+ 404.0894, found 404.0893. Anal. Calc'd for C21H18F2O4S (0.24 H2O): C, 61.70; H, 4.51. Found: C, 61.69; H, 4.56.

Sources & evidence

ORD record
ord-5f57d7eeebe24300abd45f79f9f9d5ee
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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