Phenylboronic Acid → (3-([5-(phenyl)-furan-2-carbonyl]-amino)-phenyl)-acetic Acid Methyl Ester

HRID 1444235Notes

Reaction equation

HRID 1444235 reaction equation
[CH3:1][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.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:1][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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:18]=2)=[O:13])[CH:6]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 59654700(3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl)-acetic Acid Methyl Ester

Product 1

HCID 59654656(3-([5-(phenyl)-furan-2-carbonyl]-amino)-phenyl)-acetic Acid Methyl Ester

Procedure

Methyl ester (16) (500 mg, 1.48 mmol) was coupled to phenylboronic acid (150 mg, 1.23 mmol) using Method E. The crude compound was purified by column chromatography, eluting with a stepped gradient of 20-25% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude compound was purified by column chromatography
  2. washeluting with a stepped gradient of 20-25% EtOAc in heptane

Sources & evidence

ORD record
ord-f9442a8a47344e77a3a4ab7da48ccf27
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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