Water → HCID 14032662, compound

HRID 845668Notes

Reaction equation

HRID 845668 reaction equation
[N:1]#[C:2]Br.C(=O)([O-])[O-].[K+].[K+].[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[N:15]=[C:14]2[CH:26]1[CH2:31][CH2:30][N:29](C)[CH2:28][CH2:27]1.O>CS(C)=O>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[N:15]=[C:14]2[CH:26]1[CH2:31][CH2:30][N:29]([C:2]#[N:1])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14183056HCID 14183056, compound

Product 1

HCID 14032662HCID 14032662, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of cyanogen bromide (4.05 g, 0.038 moles) and potassium carbonate (6.2 g, 0.045 moles) in dimethylsulfoxide (75 ml) was added dropwise a solution of 5-fluoro-1-phenyl-3-(1-methyl-4-piperidinyl)-1H-indazole (11.0 g, 0.036 moles) free base of Example 111(b) in hot dimethylsulfoxide (75 ml). The reaction was stirred at ambient temperature for 28 hours and then poured into water. The product was extracted (dichloromethane), dried (MgSO4) and concentrated to yield 10.8 g of an oil which crystallized upon standing. The product was recrystallized twice from isopropyl alcohol-ether and once from isopropyl alcohol which yielded 3.8 g (33%) of the 4-(5-fluoro-1-phenyl-1H-indazol-3-yl)piperidine-1-carbonitrile, m.p. 137°-139°.

Workup

  1. extractionThe product was extracted (dichloromethane)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7fd8f0a41c884d728384c9063723441c
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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