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

HRID 1747978

反応式

HRID 1747978 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]([CH3:39])[CH:34]=1>[Cu]I.CS(C)=O>[CH3:39][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 122683-IodotolueneHCID 62657Potassium Phosphate, TribasicHCID 667484774-(2-Aminopyridin-3-yl)phenol

生成物 1

HCID 667479923-(4-(3-Methylphenoxy)phenyl)pyridin-2-amine収率 68.9%

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
130 °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-methylbenzene (703 mg) and DMSO (8 mL). The mixture was stirred at 130° C. under nitrogen for 5 hr. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc). Water was added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) to give the title compound (511.5 mg) as a yellow solid.

後処理

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. additionWater was added
  4. washthe extracted organic layer was washed with brine
  5. additionSilica-gel was added to the organic layer
  6. customthe volatiles were removed in vacuo
  7. customwas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)

出典と根拠

ORDレコード
ord-e9196fa7ceb34b1780b178280619d272
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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