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

HRID 13144
Notes
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Reaction equation

HRID 13144 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

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

Conditions

Temperature
125 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e28520b5e84c42ad8fef41126721be9b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728030B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes