(4-Methoxyphenyl)boronic acid → HCID 69440473, compound

HRID 1948228Notes

Reaction equation

HRID 1948228 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH:12]=[C:11](Br)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:8]2=[O:18])=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:8]2=[O:18])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 69345221HCID 69345221, compound

Product 1

HCID 69440473HCID 69440473, compoundYield 82%

Procedure

According to Scheme 3 Method A: The title compound was prepared from methyl 1-(4-chlorobenzyl)-5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate (1 eq, 7.00 mmol, 2.50 g) and 4-methoxyphenyl boronic acid (1.5 eq, 11.0 mmol, 1.60 g) according to the procedure described for Example 1 Step 3. Reaction conditions: 4 hours at 80° C. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 80 g SiO2) using CH2Cl2/AcOEt 80/20 and by recrystallization with Et2O/pentane to afford methyl 1-(4-chlorobenzyl)-5-(4-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (5.74 mmol, 2.22 g, 82%) as a beige solid.

Workup

  1. customReaction conditions
  2. custom4 hours
  3. customat 80° C
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 80 g SiO2)
  5. customby recrystallization with Et2O/pentane

Sources & evidence

ORD record
ord-a0e7e11cb1d04ebda1f6afb6c08e0a81
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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