4-(Cyanomethyl)benzeneboronic acid → 2-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetonitrile

HRID 1948221Notes

Reaction equation

HRID 1948221 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)#[N:2].[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][N:19]2[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:20]2=[O:26])=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][N:19]2[C:20](=[O:26])[CH:21]=[CH:22][C:23]([C:7]3[CH:8]=[CH:9][C:4]([CH2:3][C:1]#[N:2])=[CH:5][CH:6]=3)=[CH:24]2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 27733424-(Cyanomethyl)benzeneboronic acidHCID 603727735-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-one

Product 1

HCID 693455142-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetonitrileYield 100%

Procedure

According to Scheme 3 Method A: The title compound was synthesized as described in Example 2 Step 2 using 4-(cyanomethyl)phenyl boronic acid (1.5 eq, 0.50 mmol, 80.9 mg) and 1-(4-chlorobenzyl)-5-bromopyridin-2(1H)-one (1 eq, 0.33 mmol, 0.10 g, Example 2 Step 1) as substrates. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt to afford 2-(4-(1-(4-chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetonitrile as a yellow solid (0.33 mmol, 110 mg, 98%).

Workup

  1. customThe title compound was synthesized
  2. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-4d3a9bd8e1ce400cb9617a50b54f92de
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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