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Hydrogen Peroxide → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-[(3,4-difluorobenzyl)oxy]nicotinamide

HRID 916979
ノート
印刷プレビュー

反応式

HRID 916979 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)[N:9]=1.C(O)(C(F)(F)F)=[O:34].[OH-].[K+].OO>O.C(O)C.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:15]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[CH:14][C:11]([C:12]([NH2:13])=[O:34])=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)[N:9]=1
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

8

反応物 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 443904852-(3,4-Difluorobenzyloxy)-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

生成物 1

HCID 589615746-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-[(3,4-difluorobenzyl)oxy]nicotinamide

試薬・触媒・溶媒 3

HCID 702
Ethanol
溶媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

To the product of Step D Example 129 (30.0 mg, 0.0516 mmol, material in the TFA salt form) was added 1,4-dioxane (4 mL), ethanol (0.5 mL), KOH (0.272 mg, 4.92 mmol), H2O (0.6 mL) and H2O2 (0.21 g). The reaction was heated to 95° C. for 22 hours. The solution was concentrated and the residue was dissolved in ethyl acetate before washing with water, drying (Na2SO4) and concentrating. The residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel) eluting with 10.5% ethyl acetate/dichloromethane affording the product. MS (electrospray) m/e 485.2 MH+ (Rt=4.2 min LC/MS).

後処理

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washbefore washing with water
  4. dry with materialdrying (Na2SO4)
  5. concentrationconcentrating
  6. customThe residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel)
  7. washeluting with 10.5% ethyl acetate/dichloromethane affording the product

出典と根拠

ORDレコード
ord-94f8fbdd9ca34b1fa4f5ea28b171dd76
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07271266B2

反応ノート

読み込み中…

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