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

HRID 1444339Notes

Reaction equation

HRID 1444339 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-59b1ca831326429f9c0eb52456e29462
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

Loading…