(4-Methoxy-3-methylphenyl)boronic acid → HCID 10739009, compound

HRID 1839950Notes

Reaction equation

HRID 1839950 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:27]=[CH:26][C:25](B(O)O)=[CH:24][C:23]=1[CH3:31]>>[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:26]=[CH:27][C:22]([O:21][CH3:20])=[C:23]([CH3:31])[CH:24]=2)=[CH:7][C:6]=1[F:8]

Participants

3

Reactant 2

HCID 2773487(4-Methoxy-3-methylphenyl)boronic acidHCID 117919231-Bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene

Product 1

HCID 10739009HCID 10739009, 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-methyl-4-methoxyphenylboronic acid (Step 2) to give 1,2-difluoro-4-(4-methoxy-3-methylpheny)-5-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 160.5-161.5° C.; NMR (CDCl3) δ 2.11 (S, 3H), 3.04 (S, 3H), 3.79 (S, 3H), 6.63 (d, J=9 Hz, 1H), 6.74 (dd, J=2, 9 Hz, 1H), 6.85 (d, J=2 Hz, 1H), 7.15-7.27 (m, 3H), 7.30 (d, J=8 Hz, 1H), 7.80 (d, J=8 Hz, 2H); MS (FAB) m/z 395 (M+Li)+; HRMS calc'd for M+ 388.0945, found 388.0940. Anal. for C21H18F2O3S: C, 64.94; H, 4.67; F, 9.78. Found: C, 64.59; H, 4.84; F, 9.52.

Sources & evidence

ORD record
ord-80a49d6978d54e8f90df4254628e69ac
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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