4-Carboxyphenylboronic Acid → HCID 58043290, compound

HRID 1618016Notes

Reaction equation

HRID 1618016 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[Cl: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]>>[Cl: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 58043461HCID 58043461, compound

Product 1

HCID 58043290HCID 58043290, compound

Procedure

The title compound was prepared in analogy to example 166, from (E)-5-{3-(4-bromo-phenyl)-3-(2-chloro-4-fluoro-phenyl)-1-(hydroxyimino)-propyl}-1-methyl-1H-pyridin-2-one (example 410) and 4-carboxyphenylboronic acid (CAS RN 14047-29-1). The compound was purified by silica gel chromatography using a MPLC system eluting with a gradient of dichlormethane:methanol (100:0 to 90:10). The resulting yellow solid was purified by preparative HPLC (phenomenex gemini column) with a gradient of acetonitrile:water (10:90 to 95:5) followed by another preparative HPLC purification (Reprosil Chiral-NR column) using 80% n-heptane:20% EtOH (containing 0.5% formic acid) as eluant to give the desired compound as a colourless solid, MS (ESI+): m/z=505.1 ([M+H]+).

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of dichlormethane:methanol (100:0 to 90:10)
  3. customThe resulting yellow solid was purified by preparative HPLC (phenomenex gemini column) with a gradient of acetonitrile:water (10:90 to 95:5)
  4. customfollowed by another preparative HPLC purification (Reprosil Chiral-NR column)

Sources & evidence

ORD record
ord-4ca41a21b6d24719884e44370148b208
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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