Acetonitrile → [4-(6-Fluoro1H-indazol-3-yl)-1-piperazinyl]acetonitrile

HRID 1601324Notes

Reaction equation

HRID 1601324 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.[Na+].[CH3:22][C:23]#[N:24]>O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:12][CH2:13][N:14]([CH2:22][C:23]#[N:24])[CH2:15][CH2:16]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 98158716-fluoro-3-piperazin-1-yl-1H-indazole

Product 1

HCID 15337664[4-(6-Fluoro1H-indazol-3-yl)-1-piperazinyl]acetonitrileYield 999.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperazinyl)-1H-indazole (6.0 g, 2.7 mmol), NaHCO3 (2.5 g, 3.0 mmol) chloroacetonitrile (2.5 g, 3.3 mmol) and CH3CN (150 mol) was stirred at reflux under N2 for 18 hours. The cooled reaction was poured into H2O and the aqueous solution was extracted with EtOAc. The EtOAc extract was washed with H2O, washed with brine, dried with MgSO4 and concentrated to yield 7.0 g of a tan solid. A 1.3 g sample was recrystallized from EtOAc to yield 0.65 g of a beige solid, m.p. 154-156° C.

Workup

  1. temperatureat reflux under N2 for 18 hours
  2. customThe cooled reaction
  3. extractionthe aqueous solution was extracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-90111df1574b4f2db294592dcc0ffbc6
Source dataset
uspto-grants-1999_11
Patent number
US05977113

Reaction notes

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