Butyronitrile → (alphaS,betaR)-beta-{[1-(3-Pyridyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamine

HRID 13135

Reaction equation

HRID 13135 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.I[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[N:17]=[CH:16]2.C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)CCC>[Cu]I>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([N:18]2[C:19]3[C:15](=[CH:14][C:13]([O:10][C@H:3]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)[C@H:2]([CH3:1])[NH2:11])=[CH:21][CH:20]=3)[CH:16]=[N:17]2)[CH:23]=1

Participants

6

Reactant 4

HCID 8008ButyronitrileHCID 10297PhenylpropanolamineHCID 10796Cesium carbonateHCID 597865715-iodo-1-pyridin-3-yl-1H-indazole

Product 1

HCID 66812930(alphaS,betaR)-beta-{[1-(3-Pyridyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamineYield 27%

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), 5-iodo-1-(3-pyridyl)-1H-indazole (1.08 g, 33.37 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). 307.8 mg (27%) 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-f0b9853f3efa4013b552f76ed7d1b0c9
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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