Butyronitrile → Methyl 4-{5-[(1R,2S)-2-amino-1-phenylpropoxy]-1H-indazole-1-yl}benzoate

HRID 13140

Reaction equation

HRID 13140 reaction equation
[CH3:1][C@H:2]([NH2:11])[C@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:12][O:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:29]3[C:24](=[CH:25][C:26](I)=[CH:27][CH:28]=3)[CH:23]=[N:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)CCC>[Cu]I>[NH2:11][C@@H:2]([CH3:1])[C@@H:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[O:10][C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[N:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]([O:13][CH3:12])=[O:31])=[CH:16][CH:17]=1)[N:22]=[CH:23]2

Participants

6

Reactant 4

HCID 8008ButyronitrileHCID 10297PhenylpropanolamineHCID 10796Cesium carbonateHCID 66812731Methyl-4-(5-iodoindazole-1-yl)-benzoate

Product 1

HCID 66812703Methyl 4-{5-[(1R,2S)-2-amino-1-phenylpropoxy]-1H-indazole-1-yl}benzoateYield 16.4%

Reagents, catalysts & solvents 1

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

Procedure

(1R,2S)-Norephedrine (500 mg, 3.31 mmol), methyl-4-(5-iodoindazole-1-yl)-benzoate (1.28 g, 3.37 mmol), cesiumcarbonate (2.15 g, 6.61 mmol), copper (I)-iodide (314.9 mg, 1.65 mmol) and butyronitrile (2 mL) are stirred in a glass pressure tube at 120° C. for 20 h. The reaction mixture is filtered via a glass microfibre filter, the solvent evaporated and the residue purified by chromatography (silicagel, eluents: dichloromethane/methanol). 217.9 mg (16.4%) of the title compound are obtained.

Workup

  1. filtrationThe reaction mixture is filtered via a glass microfibre
  2. filtrationfilter
  3. customthe solvent evaporated
  4. customthe residue purified by chromatography (silicagel, eluents: dichloromethane/methanol)

Sources & evidence

ORD record
ord-a1859bc334c54a22a0996c07c8da5b3b
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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