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Triphenylarsine → 4-[2-(4-Pyrimidin-2-yl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

HRID 14608
ノート
印刷プレビュー

反応式

HRID 14608 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:21])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].C([Sn](CCCC)(CCCC)[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1)CCC.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:21])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:16][CH:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4]
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 3

HCID 11773TriphenylarsineHCID 27632512-(Tributylstannyl)pyrimidineHCID 686873304-[2-(4-Iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

生成物 1

HCID 686874114-[2-(4-Pyrimidin-2-yl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester収率 59.7%

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To 4-[2-(4-Iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (77.6 mg) in DMF (1 mL) was added 2-(tributylstannyl)pyrimidine (74.1 mg), tris(dibenzylideneacetone)-di-Palladium, triphenylarsine (27 mg) and copper (I) iodide (3.2 mg) and the reaction mixture was stirred at 90° C. overnight. The reaction mixture was then allowed to cool to room temperature and was concentrated in vacuo. To the residue was then added ethylacetate (4 mL) and an aqueous solution of potassium fluoride (30%) and the mixture was stirred rigorously for one hour. Then the solid was filtered off and the biphasic filtrate was separated. The organic layer was dried with sodium sulfate and concentrated in vacuo. The residue was then purified by column chromatography to yield the title compound (41 mg, 59%).

後処理

  1. temperatureto cool to room temperature
  2. concentrationwas concentrated in vacuo
  3. stirringadded ethylacetate (4 mL) and an aqueous solution of potassium fluoride (30%) and the mixture was stirred rigorously for one hour
  4. filtrationThen the solid was filtered off
  5. customthe biphasic filtrate was separated
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by column chromatography

出典と根拠

ORDレコード
ord-f00d233ece4c4ef6842b8ecf31910015
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07732452B2

反応ノート

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