[(E)-2-(2,4-difluorophenyl)ethenyl]boronic acid → Methyl 2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzoate

HRID 1351680

Reaction equation

HRID 1351680 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1/[CH:29]=[CH:30]/B(O)O>>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1/[CH:29]=[CH:30]/[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21099524[(E)-2-(2,4-difluorophenyl)ethenyl]boronic acidHCID 21099525Methyl 2-[(4-bromophenyl)sulfonyl]benzoate

Product 1

HCID 11509873Methyl 2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzoate

Procedure

The title compound was prepared according to the method described in Example 138, Step 3 using methyl 2-[(4-bromophenyl)sulfonyl]benzoate (Step 1) in place of (1S)-1-[2-({4-bromo-3-methylphenyl}sulfonyl)phenyl]ethanol and [(E)-2-(2,4-difluorophenyl)vinyl]boronic acid (Step 2) in place of [(E)-2-(4-fluorophenyl)vinyl]boronic acid. δH (500 MHz, d6 DMSO): 8.22–8.20 (1H, m), 7.94–7.80 (7H, m), 7.69–7.63 (1H, m), 7.44 (1H, d, J 16.4), 7.39 (1H, d, J 16.4), 7.35–7.30 (1H, m), 7.19–7.15 (1H, m), 3.87 (3H, s). m/z (ES+) 383 [(M−MeO)+].

Sources & evidence

ORD record
ord-c2f6954e4f874230955bebc1654e883c
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Linked notes

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