4-Formylphenylboronic Acid → HCID 22341441, compound

HRID 584997Notes

Reaction equation

HRID 584997 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24](Br)=[CH:23][C:10]=1[CH2:11][N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29]>>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]([C:33]2[CH:34]=[CH:35][C:30]([CH:28]=[O:29])=[CH:31][CH:32]=2)=[CH:23][C:10]=1[CH2:11][N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 22341492HCID 22341492, compound

Product 1

HCID 22341441HCID 22341441, compound

Procedure

In a manner similar to that of Example 1(e), by reacting 8 g (18.5 mmol) of N-(2-benzyloxy-5-bromo benzyl)-N-methyloctanamide and 3.6 g (24 mmol) of 4-formylbenzene boronic acid, and after purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (8/2), 5.8 g (69%) of the expected product are obtained in the form of a white solid.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a heptane/ethyl acetate mixture (8/2), 5.8 g (69%) of the expected product
  3. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-835ebeebe7f04a8bbc4624e5b2b38e5a
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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