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

HRID 1948222
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HRID 1948222 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a8c6a11768374e6da479c06759ada897
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399493B2

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