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Dimethylformamide → methyl (E)-3-(4-chloro-1-(2-chloro-4-(2-furyl)benzyl)-2-methylimidazol-5-yl)-2-propenate

HRID 1828813
ノート
印刷プレビュー

反応式

HRID 1828813 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([CH3:22])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][C:15]=2[Cl:21])[C:6]=1/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10].[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:22])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:24]3[O:23][CH:27]=[CH:26][CH:25]=3)=[CH:16][C:15]=2[Cl:21])[C:6]=1/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 15524214methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenate

生成物 1

HCID 86760099methyl (E)-3-(4-chloro-1-(2-chloro-4-(2-furyl)benzyl)-2-methylimidazol-5-yl)-2-propenate収率 110.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of tetrakis(triphenylphosphine)palladium(0) (89 mg), methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenate (350 mg), 2-furylboronic acid (135 mg), potassium carbonate powder (321 mg) and N,N-dimethylformamide (3.5 ml) was stirred under a nitrogen atmosphere at 80° C. for 4 hr. The reaction mixture was allowed to cool to room temperature and water was added. The precipitate was collected by filtration. The precipitate was dissolved in chloroform, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (chloroform/ethyl acetate=10/1) to give methyl (E)-3-(4-chloro-1-(2-chloro-4-(2-furyl)benzyl)-2-methylimidazol-5-yl)-2-propenate (336 mg) as a pale-yellow powder.

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in chloroform
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (chloroform/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-5da25c48612a4b11aaa53eff348cd0a1
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07060721B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート