Acetonitrile → N-[2-[4-(6-fluoro1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimide

HRID 1080319Notes

Reaction equation

HRID 1080319 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].CC#N>O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:12][CH2:13][N:14]([CH2:24][CH2:25][N:26]4[C:30](=[O:31])[C:29]5=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]5[C:27]4=[O:36])[CH2:15][CH2:16]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 98158716-fluoro-3-piperazin-1-yl-1H-indazole

Product 1

HCID 18467209N-[2-[4-(6-fluoro1H-indazol-3-yl)-1-piperazinyl]ethyl]phthalimideYield 56.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperazinyl)-1H-indazole (4.0 g, 18 mmol), K2CO3 (2.7 g, 20 mmole), N-(2-bromoethyl)phthalimide (4.8 g, 19 mmole) and CH3CN (100 ml) was stirred at reflux under N2 for 4 hours. After standing at ambient temperature for 65 hours, the reaction was poured into H2O. The resultant solid was collected to yield 4.0 g of a yellow powder. The product was recrystallized twice from ethanol to yield 3.5 g (50%) of a beige powder m.p.=220°-223 ° C.

Workup

  1. temperatureat reflux under N2 for 4 hours
  2. customThe resultant solid was collected

Sources & evidence

ORD record
ord-08b94691b0e74fe39c199f8ff5f78217
Source dataset
uspto-grants-1996_12
Patent number
US05580891

Reaction notes

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