Picolinic acid → 3-(4-(3-Methoxyphenoxy)phenyl)pyridin-2-amine

HRID 1747947

反応式

HRID 1747947 の反応式
N1C=CC=CC=1C(O)=O.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:15][CH:14]=[CH:13][N:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=1>[Cu]I.CS(C)=O>[CH3:40][O:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[C:11]([NH2:10])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:18][CH:19]=1

参加物

7

反応物 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 69839Benzene, 1-iodo-3-methoxy-HCID 667484774-(2-Aminopyridin-3-yl)phenol

生成物 1

HCID 667488603-(4-(3-Methoxyphenoxy)phenyl)pyridin-2-amine収率 44.5%

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

Copper(I) iodide (102 mg) was added to a mixture of picolinic acid (66.1 mg), 4-(2-aminopyridin-3-yl)phenol (500 mg), tripotassium phosphate (1710 mg), 1-iodo-3-methoxybenzene (754 mg) and DMSO (8 mL). The mixture was stirred at 120° C. under nitrogen for 6 hr. The insoluble material was removed by silica-filtration with EtOAc, and the filtrate was extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (349 mg) as a yellow solid.

後処理

  1. customThe insoluble material was removed by silica-filtration with EtOAc
  2. extractionthe filtrate was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

出典と根拠

ORDレコード
ord-63a74fb538794ce58abf843522b37510
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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