(3,5-Difluorophenyl)boronic acid → HCID 59654603, compound

HRID 1717121Notes

Reaction equation

HRID 1717121 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[O:15][C:16](Br)=[CH:17][CH:18]=2)=[O:13])[CH:6]=1.[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([F:28])[CH:27]=1>>[F:21][C:22]1[CH:23]=[C:24]([C:16]2[O:15][C:14]([C:12]([NH:11][C:7]3[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:20])[CH:10]=[CH:9][CH:8]=3)=[O:13])=[CH:18][CH:17]=2)[CH:25]=[C:26]([F:28])[CH:27]=1

Participants

3

Reactant 2

HCID 2734338(3,5-Difluorophenyl)boronic acidHCID 59654700(3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl)-acetic Acid Methyl Ester

Product 1

HCID 59654603HCID 59654603, compound

Procedure

The furyl bromide (16) (100 mg, 0.30 mmol) was coupled to 3,5-difluoro-phenylboronic acid (48 mg, 0.30 mmol) using Method E. During this reaction, hydrolysis occurred. The residue was extracted using Work-up E1 to give the acid. The residue was purified by column chromatography eluting with 20% heptane:75% EtOAc:5% AcOH to give the title compound.

Workup

  1. customDuring this reaction, hydrolysis
  2. extractionThe residue was extracted
  3. customto give the acid
  4. customThe residue was purified by column chromatography
  5. washeluting with 20% heptane

Sources & evidence

ORD record
ord-f9fbb68c412647d480e1737ff55cca95
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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