Water → HCID 14032638, compound

HRID 845648Notes

Reaction equation

HRID 845648 reaction equation
[N:1]#[C:2]Br.C(=O)([O-])[O-].[K+].[K+].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]2[CH2:31][CH2:30][N:29](C)[CH2:28][CH2:27]2)=[N:18]1.O>CS(C)=O>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]2[CH2:31][CH2:30][N:29]([C:2]#[N:1])[CH2:28][CH2:27]2)=[N:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14032538HCID 14032538, compound

Product 1

HCID 14032638HCID 14032638, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of cyanogen bromide (15.5 g, 0.146 moles) and potassium carbonate (23.7 g, 0.167 moles) in dimethylsulfoxide (DMSO) [300 ml]was added dropwise a solution of 1-(2-fluorophenyl)-3-(1-methyl-4-piperidinyl)-1H-indazole, the free base of example 36, (42.0 g, 0.137 moles) in dimethylsulfoxide (40 ml). The reaction temperature rose to 36° C. and the mixture was stirred at ambient temperature for 2.5 days. The reaction mixture was then poured into H2O and the product extracted with ether. The ether was dried (MgSO4) and concentrated which left 40 g of a solid. The product was recrystallized 5 times from isopropyl alcohol which yielded 13.6 g (31%) of 4-[1-(2-fluorophenyl)-1H-indazol-3-yl]piperidine-1-carbonitrile, m.p. 119°-121° C.

Workup

  1. customrose to 36° C.
  2. extractionthe product extracted with ether
  3. dry with materialThe ether was dried (MgSO4)
  4. concentrationconcentrated which
  5. waitleft 40 g of a solid
  6. customThe product was recrystallized 5 times from isopropyl alcohol which

Sources & evidence

ORD record
ord-46c5693335cc46daa7a871c2d9df113f
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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