Dimethylformamide → HCID 57566815、化合物

HRID 1819344ノート

反応式

HRID 1819344 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:24]1[CH:25]=[C:26]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:28][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C=O)C>[Cu]I.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 125741-Iodo-3-nitrobenzeneHCID 62657Potassium Phosphate, TribasicHCID 145371514-[3-(Benzyloxy)-4-methoxyphenyl]pyrrolidin-2-one

生成物 1

HCID 57566815HCID 57566815、化合物収率 57%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a round bottom flask was added 4-(3-benzyloxy-4-methoxyphenyl)-pyrrolidin-2-one (1.76 g, 5.9 mmol), 3-iodonitrobenzene (2.64 g, 10.6 mmol), K3PO4 (2.79 g, 13 mmol), trans-cyclohexanediamine (50 μL), DMF (8 mL) and dioxane (8 mL). The mixture was stirred under N2 for 5 min before the addition of CuI (150 mg). After heating to 110° C. for 20 h, the mixture was cooled to r.t. After filtration, the reaction mixture was diluted with EtOAc (100 mL), washed with saturated NH4Cl, brine and dried over Na2SO4. Concentration and purification by column chromatography on silica gel (EtOAc:hexane=1:3) gave 1.4 g of the desired product. Yield: 57%.

後処理

  1. temperaturethe mixture was cooled to r.t
  2. filtrationAfter filtration
  3. additionthe reaction mixture was diluted with EtOAc (100 mL)
  4. washwashed with saturated NH4Cl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration and purification by column chromatography on silica gel (EtOAc:hexane=1:3)

出典と根拠

ORDレコード
ord-264eda41177140659e93766d32a0870e
出典データセット
uspto-grants-2009_10
特許番号
US07601742B2

反応ノート

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