Butyronitrile → 1-Methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethylamine

HRID 1098906

反応式

HRID 1098906 の反応式
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[N:6]=[CH:5]2.[CH3:17][C@H:18]([NH2:27])[C@H:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(#N)CCC.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[CH3:17][CH:18]([NH2:27])[CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:26][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[N:6]=[CH:5]2

参加物

6

反応物 4

HCID 8008ButyronitrileHCID 10297PhenylpropanolamineHCID 10796Cesium carbonateHCID 593397925-iodo-1-pyridin-2-yl-1H-indazole

生成物 1

HCID 668129981-Methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethylamine収率 16.3%

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

反応条件

温度
125 °C

実験手順

5-Iodo-1-pyridin-2-yl-1H-indazole (118b, 81 mg, 0.25 mmol), (1R,2S)-(−)-norephedrine (119 mg, 0.79 mmol) and butyronitrile (3 ml) were charged in a 7 ml vial. Copper(I) iodide (5.8 mg, 0.1 mol %) and cesium carbonate (261 mg, 0.8 mmol) were added, the vial was sealed and the solution was stirred (magnetic bar) at 125° C. for 2 h. Inorganic material was filtered off, and washed with ethyl acetate. The ethyl acetate phase was collected and concentrated and purified on silica with methanol:ethyl acetate 0:100 to 30:70 over 45 min. Pure fractions were pooled and concentrated to give 14 mg (16%) of 1-methyl-2-phenyl-2-(1-pyridin-2-yl-1H-indazol-5-yloxy)-ethylamine.

後処理

  1. customthe vial was sealed
  2. filtrationInorganic material was filtered off
  3. washwashed with ethyl acetate
  4. customThe ethyl acetate phase was collected
  5. concentrationconcentrated
  6. custompurified on silica with methanol:ethyl acetate 0:100 to 30:70 over 45 min
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-421f83de2e124eec958255a2458ab25e
出典データセット
uspto-grants-2012_03
特許番号
US08143290B2

関連ノート

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