Water → HCID 14823466, compound

HRID 1461831Notes

Reaction equation

HRID 1461831 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].BrC#[N:35].O>CS(C)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:20]3[CH2:21][CH2:22][N:23]([C:26]#[N:35])[CH2:24][CH2:25]3)=[N:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14823465HCID 14823465, compound

Product 1

HCID 14823466HCID 14823466, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture, under N2 of 6-fluoro-1-phenylsulfonyl-3-(4-methyl-1-piperazinyl)-1H-indazole (30.0 g, 0.86 mol) of Example 31c, K2CO3 (4.7 g, 0.086 mol) and dimethyl sulfoxide (DMSO) [250 ml] was added, dropwise, BrCN (9.1 g, 0.086 mol) dissolved in DMSO (50 ml). The reaction was stirred at ambient temperature for 2 hours and water was added. The resultant solid was collected and taken up in CH2Cl2, and after washing the organic layer with H2O, drying (K2CO3) and concentrating there remained 25.3 g of the target compound. A sample (5.0 g) was removed and recrystallized from ethyl acetate (twice) to afford 2.3 g (35%) of 4-(6-fluoro-1-phenylsulfonyl-1H-indazol-3-yl)-1-piperazine carbonitrile m.p. 178°-180° C.

Workup

  1. customThe resultant solid was collected
  2. washafter washing the organic layer with H2O
  3. dry with materialdrying (K2CO3)
  4. concentrationconcentrating there remained 25.3 g of the target compound
  5. customA sample (5.0 g) was removed
  6. customrecrystallized from ethyl acetate (twice)

Sources & evidence

ORD record
ord-b0236b1cf9fd4fc98ce8e2748ed16124
Source dataset
uspto-grants-1991_12
Patent number
US05077405

Reaction notes

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