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

HRID 14608

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

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 24350Copper(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
特許番号
US07732452B2

関連ノート

読み込み中…