Water → 4-[1-(Phenylsulfonyl)-1H-indazol-3-yl]-1-piperazinecarbonitrile

HRID 357330Notes

Reaction equation

HRID 357330 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[N:9]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[N:32]#CBr.O>CS(C)=O>[C:20]1([S:17]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([N:5]3[CH2:4][CH2:3][N:2]([C:1]#[N:32])[CH2:7][CH2:6]3)=[N:9]2)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 148234251-(Benzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indazole

Product 1

HCID 148234434-[1-(Phenylsulfonyl)-1H-indazol-3-yl]-1-piperazinecarbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of 3-(4-methyl-1-piperazinyl)-1-phenylsulfonyl 1H-indazole (237 g, 0.67 mole), K2CO3 (102 g, 0.74 mole) and dimethylsulfoxide (DMSO, 2000 ml), under nitrogen, was added cyanogen bromide (72 g, 0.68 mmol) dissolved in DMSO (525 ml). The reaction was stirred at ambient temperature for 5.5 hours and was then poured into H2O (7 l). The solid, which precipitated from solution, was collected by filtration and was washed well with H2O affording 168 g (68%) of product. A 5.2 g sample was recrystallized twice from ethanol-H2O yielding 4.0 g of 4-[1-(phenylsulfonyl)-1H-indazol-3-yl]-1-piperazinecarbonitrile, m.p.=178°-180° C.

Workup

  1. customThe solid, which precipitated from solution
  2. filtrationwas collected by filtration
  3. washwas washed well with H2O affording 168 g (68%) of product
  4. customA 5.2 g sample was recrystallized twice from ethanol-H2O yielding 4.0 g of 4-[1-(phenylsulfonyl)-1H-indazol-3-yl]-1-piperazinecarbonitrile, m.p.=178°-180° C.

Sources & evidence

ORD record
ord-ea9e6373f1054338b8a030d408ef3188
Source dataset
uspto-grants-1998_11
Patent number
US05840727

Reaction notes

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