Toluene → HCID 66524905, compound

HRID 2411237Notes

Reaction equation

HRID 2411237 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.CN(C)C=O>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:5]2[C:6]([C:7]#[N:8])=[CH:9][C:2]([Br:1])=[CH:3][N:4]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 219482695-Bromo-2-chloronicotinonitrile

Product 1

HCID 66524905HCID 66524905, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-bromo-2-chloronicotinonitrile (1.00 g), 1-Boc-piperazine (0.94 g) and potassium carbonate (1.27 g) were added toluene (4.5 mL) and N,N-dimethylformamide (10 mL), and the mixture was stirred at 100° C. for 4 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.52 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0baf11815a324ef1ba4c79fc35a23eee
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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