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Propargyl alcohol → N-(4-chlorobenzyl)-2-(3-hydroxyprop-1-ynyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 982706
ノート
印刷プレビュー

反応式

HRID 982706 の反応式
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:21])[C:12]3[S:19][C:18](I)=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:24]([OH:27])[C:25]#[CH:26]>CN(C=O)C.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:21])[C:12]3[S:19][C:18]([C:26]#[C:25][CH2:24][OH:27])=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 22563223N-(4-chlorobenzyl)-2-iodo-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

生成物 1

HCID 10000250N-(4-chlorobenzyl)-2-(3-hydroxyprop-1-ynyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide収率 68.7%

試薬・触媒・溶媒 2

HCID 498840Bis(benzonitrile)palladium chloride触媒
HCID 6228
Dimethylformamide
溶媒

実験手順

A mixture of N-(4-chlorobenzyl)-2-iodo-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (0.20 g, 0.44 mmol), Pd(PhCN)2Cl2 (10 mg) CuI (7 mg) Et3N (1 mL) and propargyl alcohol (0.036 g, 0.66 mmol) in DMF was stirred at ambient temperature overnight. The solvent was removed and the residue partitioned between H2O and CH2Cl2 (100 mL each). The layers were shaken, the organic layer separated and dried over MgSO4. The solvents were removed in vacuo and the residue purified via flash column chromatography (eluant 5% MeOH/CH2Cl2) to afford 0.117 g title compound as a white solid.

後処理

  1. customThe solvent was removed
  2. customthe residue partitioned between H2O and CH2Cl2 (100 mL each)
  3. stirringThe layers were shaken
  4. customthe organic layer separated
  5. dry with materialdried over MgSO4
  6. customThe solvents were removed in vacuo
  7. customthe residue purified via flash column chromatography (eluant 5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-9a4e32aec016475bafe0df76622b7dea
出典データセット
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06861438B2

反応ノート

読み込み中…

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