Cyanogen Bromide → HCID 14032617, compound

HRID 867685Notes

Reaction equation

HRID 867685 reaction equation
Cl.[C:2]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[N:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[N:32]#CBr>C(Cl)(Cl)Cl>[C:2]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]#[N:32])[CH2:21][CH2:20]2)=[N:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14032515HCID 14032515, compound

Product 1

HCID 14032617HCID 14032617, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A sample of 8.4 g of 1-benzoyl-3-(1-methyl-4-piperidinyl)-1H-indazole hydrochloride was converted to its free base and the base was dissolved in 135 ml of chloroform. The solution was stirred and 4.0 g of potassium carbonate was added followed by 2.7 g of cyanogen bromide. The reaction mixture was stirred under reflux for 16 hrs. The mixture was filtered, and the solvent was removed in vacuo. The mixture was chromatographed on a high-pressure column chromatography apparatus (silica gel), eluting with 0.3% methanol/dichloromethane. Evaporation of the appropriate fraction followed by recrystallization from toluene hexane yielded 2.2 g (28%) of the product, mp 144°-146° C.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 16 hrs
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed in vacuo
  5. customThe mixture was chromatographed on a high-pressure column chromatography apparatus (silica gel)
  6. washeluting with 0.3% methanol/dichloromethane
  7. customEvaporation of the appropriate fraction
  8. customfollowed by recrystallization from toluene hexane

Sources & evidence

ORD record
ord-d24fd522b36f4b7bb70dfd3790f029c4
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

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