4-Carboxyphenylboronic Acid → HCID 58043365, compound

HRID 1618011Notes

Reaction equation

HRID 1618011 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[CH2:9]/[C:10](/[C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[C:29]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)([OH:31])=[O:30]>>[F:28][C:22]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=1[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:36]=[CH:37][C:32]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=2)=[CH:3][CH:4]=1)[CH2:9]/[C:10](=[N:11]\[OH:12])/[C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1

Participants

3

Reactant 2

HCID 3121834-Carboxyphenylboronic AcidHCID 58043585HCID 58043585, compound

Product 1

HCID 58043365HCID 58043365, compound

Procedure

The title compound was prepared in analogy to example 166, from 5-{3-(4-bromo-phenyl)-3-(2,4-difluoro-phenyl)-1-[(E)-hydroxyimino]-propyl}-1-methyl-1H-pyridin-2-one (example 402) and 4-carboxyphenylboronic acid (CAS RN 14047-29-1). The compound was purified by two silica gel chromatographies using a 20 g column and a MPLC system eluting with a gradient of dichloromethane:methanol (100:0 to 70:30). Light brown foam. MS (ESI+): m/z=489.2 ([M+H]+).

Workup

  1. customThe compound was purified by two silica gel chromatographies
  2. washa MPLC system eluting with a gradient of dichloromethane:methanol (100:0 to 70:30)

Sources & evidence

ORD record
ord-891499c0572f4ecea1c6147af49b10b0
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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