Water → HCID 14032657, compound

HRID 1722170Notes

Reaction equation

HRID 1722170 reaction equation
[N:1]#[C:2]Br.C(=O)([O-])[O-].[K+].[K+].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:26]3[CH2:31][CH2:30][N:29](C)[CH2:28][CH2:27]3)=[N:18]2)=[CH:13][CH:12]=1.O>CS(C)=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:26]3[CH2:31][CH2:30][N:29]([C:2]#[N:1])[CH2:28][CH2:27]3)=[N:18]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14032568HCID 14032568, compound

Product 1

HCID 14032657HCID 14032657, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of cyanogen bromide (21.67 g, 0.204 moles) and potassium carbonate (33.2 g, 0.24 moles) in dimethyl sulfoxide (400 ml) was added dropwise a solution of 1-(4-fluorophenyl)-3-(1-methyl-4-piperidinyl)-1H-indazole (59.45 g, 0.192 moles), the free base of example 67, in hot dimethyl sulfoxide (375 ml). The reaction was stirred at ambient temperature for 4 days and then poured into H2O (500 ml). The product was extracted (dichloromethane), dried (MgSO4), and concentrated to yield 64 g of a solid. The product was recrystallized twice from isopropyl alcohol yield 35.7 g (58%) of 4-[1-(4-fluorophenyl)-1H-indazol-3-yl]piperidine-1-carbonitrile, mp 108°-110° C.

Workup

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

Sources & evidence

ORD record
ord-45519f25e44345a38031ce5d59eff083
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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