2-Methylpyridine → 3-(4-(3-Chlorophenoxy)phenyl)pyridin-2-amine

HRID 1747939ノート

反応式

HRID 1747939 の反応式
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=1.N1C=CC=CC=1C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I.O>[Cl:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 79752-MethylpyridineHCID 122691-Chloro-3-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 667484774-(2-Aminopyridin-3-yl)phenol

生成物 1

HCID 668241643-(4-(3-Chlorophenoxy)phenyl)pyridin-2-amine収率 48.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To a mixture of 4-(2-aminopyridin-3-yl)phenol (400 mg), 1-chloro-3-iodobenzene (615 mg), picoline acid (52.9 mg) and tripotassium phosphate (1368 mg) in DMSO (6 mL) was added copper (I) iodide (82.0 mg). The reaction mixture was stirred under a nitrogen atmosphere at 120° C. for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and concentrated under reduced pressure to give the title compound (307 mg) as a yellow solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2b69a7cbdb224441a3b8e67cecec420f
出典データセット
uspto-grants-2015_10
特許番号
US09150591B2

反応ノート

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