1,10-Phenanthroline → 6-(Azetidin-3-yloxy)imidazo[1,2-a]pyridine

HRID 1021312ノート

反応式

HRID 1021312 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[OH:11][CH:12]1[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(C(F)(F)F)=O>[Cu](I)I.ClCCl.O.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[NH:14]1[CH2:15][CH:12]([O:11][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[CH:7]=2)[CH2:13]1

参加物

11

反応物 5

HCID 13181,10-PhenanthrolineHCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 27643276-Iodoimidazo(1,2-a)pyridine

生成物 1

HCID 683090446-(Azetidin-3-yloxy)imidazo[1,2-a]pyridine収率 60.9%

試薬・触媒・溶媒 5

HCID 83717Copper iodide触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

6-Iodoimidazo[1,2-a]pyridine (400 mg), tert-butyl 3-hydroxyazetidine-1-carboxylate (500 mg), and toluene (2 ml) were mixed, and copper iodide (I) (40 mg), 1,10-phenanthroline (60 mg), and cesium carbonate (1 g) were added thereto, followed by stirring at 100° C. overnight. CHCl3 and water were added to the reaction mixture, and the organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The purified product thus obtained was mixed with dichloromethane (5 ml), and TFA (1.5 ml) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain 6-(azetidin-3-yloxy)imidazo[1,2-a]pyridine (189 mg).

後処理

  1. dry with materialthe organic layer was dried over Na2SO4
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  4. customThe purified product thus obtained
  5. additionwas added
  6. stirringby stirring at room temperature for 3 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

出典と根拠

ORDレコード
ord-ac65f3f823ba49ada14e78697e3c2ed4
出典データセット
uspto-grants-2014_05
特許番号
US08716470B2

反応ノート

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