2-Methylpyridine → 3-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine

HRID 1747904

反応式

HRID 1747904 の反応式
N1C=CC=CC=1C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([OH:28])=[CH:25]2)=[CH:20][CH:19]=1.Br[C:30]1[C:31]([NH2:36])=[N:32][CH:33]=[CH:34][CH:35]=1>[Cu]I.O.CS(C)=O>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([O:28][C:30]3[C:31]([NH2:36])=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:25]2)=[CH:20][CH:19]=1

参加物

8

反応物 4

HCID 79752-MethylpyridineHCID 62657Potassium Phosphate, TribasicHCID 8177002-Amino-3-bromopyridineHCID 8531737-Methoxy-2-naphthol

生成物 1

HCID 667485403-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine収率 36.1%

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
140 °C

実験手順

A mixture of picoline acid (0.427 g), tripotassium phosphate (11.04 g), copper (I) iodide (0.660 g), 7-methoxynaphthalen-2-ol (6.04 g), 3-bromopyridin-2-amine (3 g) and DMSO(50 mL) was stirred under a nitrogen atmosphere at 140° C. overnight. Water was added, and the mixture was filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and basic silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.667 g) as a pale-yellow solid.

後処理

  1. filtrationthe mixture was filtered through celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane) and basic silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-b53d972726424ce99dc08d81bbdcc283
出典データセット
uspto-grants-2015_10
特許番号
US09150591B2

関連ノート

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