Dibutyltin oxide → 5-(4-((2H-Tetrazol-5-yl)methyl)phenyl)-1-(4-chlorobenzyl)pyridin-2(1H)-one

HRID 1948222Notes

Reaction equation

HRID 1948222 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=3)=[CH:8]2)=[CH:4][CH:3]=1.C([Sn](=O)CCCC)CCC.[N:35]([Si](C)(C)C)=[N+:36]=[N-:37]>C1(C)C=CC=CC=1>[N:22]1[NH:35][N:36]=[N:37][C:21]=1[CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:9]2[CH:10]=[CH:11][C:12](=[O:13])[N:7]([CH2:6][C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:8]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 693455142-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetonitrile

Product 1

HCID 589669245-(4-((2H-Tetrazol-5-yl)methyl)phenyl)-1-(4-chlorobenzyl)pyridin-2(1H)-oneYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to Scheme 15 Method D: 2-(4-(1-(4-Chlorobenzyl)-1,6-dihydro-6-oxopyridin-3-yl)phenyl)acetonitrile (1 eq, 0.24 mmol, 0.08 g) was heated at 110° C. under nitrogen overnight with dibutyltin oxide (0.22 eq, 0.05 mmol, 0.01 g) and azidotrimethylsilane (6.0 eq, 1.43 mmol, 0.19 mL) in toluene (4 mL). The suspension was filtered and the filtrate concentrated under vacuo. The crude product was purified by chromatography on silica gel using MeOH/AcOEt 20/80 as eluent and recrystallised in diisopropyl ether to afford the title compound as a white solid (0.09 mmol, 35 mg, 39%).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate concentrated under vacuo
  3. customThe crude product was purified by chromatography on silica gel
  4. customrecrystallised in diisopropyl ether

Sources & evidence

ORD record
ord-a8c6a11768374e6da479c06759ada897
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

Loading…