Water → HCID 14032662, compound

HRID 652199Notes

Reaction equation

HRID 652199 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° C.

Workup

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

Sources & evidence

ORD record
ord-4bef5c8268da4695986bef6f945d1f2f
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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