4-Acetylphenylboronic acid → HCID 69349823, compound

HRID 1948234Notes

Reaction equation

HRID 1948234 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11](Br)[CH:10]=[CH:9][C:8]2=[O:14])=[CH:4][CH:3]=1.[C:17]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)(=[O:19])[CH3:18]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:23]3[CH:24]=[CH:25][C:20]([C:17](=[O:19])[CH3:18])=[CH:21][CH:22]=3)[CH:10]=[CH:9][C:8]2=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 37021224-Acetylphenylboronic acidHCID 603727735-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-one

Product 1

HCID 69349823HCID 69349823, compoundYield 86%

Procedure

According to Scheme 3 Method A: The title compound was prepared from 1-(4-chlorobenzyl)-5-bromopyridin-2(1H)-one (Example 2 Step 1) and 4-acetylphenylboronic acid according to the procedure described for Example 2 Step 2. Reaction conditions: 4 hours at 80° C. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 50/50 as eluent to afford 1-(4-chlorobenzyl)-5-(4-acetylphenyl)pyridin-2(1H)-one (0.29 mmol, 0.10 g, 86%) as a yellow solid.

Workup

  1. customReaction conditions
  2. custom4 hours
  3. customat 80° C
  4. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-352109047d1b445d8adc3a3568d1beba
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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