1,10-Phenanthroline → 1-{6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinyl}-5-methyl-2-pyrrolidinone

HRID 1714991ノート

反応式

HRID 1714991 の反応式
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[CH:22]=[CH:21][C:20](I)=[CH:19][N:18]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH3:38][CH:39]1[NH:43][C:42](=[O:44])[CH2:41][CH2:40]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[N:18]=[CH:19][C:20]([N:43]5[CH:39]([CH3:38])[CH2:40][CH2:41][C:42]5=[O:44])=[CH:21][CH:22]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 660555-Methyl-2-pyrrolidoneHCID 574402941H-3-Benzazepine, 3-cyclobutyl-2,3,4,5-tetrahydro-7-[(5-iodo-2-pyridinyl)oxy]-

生成物 1

HCID 104305641-{6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinyl}-5-methyl-2-pyrrolidinone収率 50%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
175 °C

実験手順

3-Cyclobutyl-7-[(5-iodo-2-pyridinyl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine (E207) (294 mg, 0.7 mmol) 1,10 phenanthroline (38 mg, 0.2 mmol), 5-methyl-2-pyrrolidinone (139 mg 1.4 mmol) were dissolved in dioxane (2 ml). Copper(I) Iodide (39 mg, 0.2 mmol) and caesium carbonate (479 mg, 1.5 mmol) were added and the mixture heated in a microwave reactor at 175° C. for 15 minutes. The mixture was cooled and filtered through celite, washing through with dichloromethane. The filtrate was concentrated in vacuo and the crude material purified by column chromatography, eluting with dichloromethane through to a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the title compound (137 mg); MS (ES+) m/e 392 [M+H]+.

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashing through with dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude material purified by column chromatography
  6. washeluting with dichloromethane through to a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

出典と根拠

ORDレコード
ord-5a853d308c2249cc84e153663b48b288
出典データセット
uspto-grants-2010_09
特許番号
US07799773B2

反応ノート

読み込み中…