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

HRID 13144

반응식

HRID 13144 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

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

반응 조건

온도
125 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e28520b5e84c42ad8fef41126721be9b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728030B2

연결된 노트

불러오는 중…