Phenylacetonitrile → HCID 70979221, compound

HRID 873326Notes

Reaction equation

HRID 873326 reaction equation
Br[C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]1([CH2:15][C:16]#[N:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+].CCOC(C)=O>CN1C(=O)CCC1.O>[Br:8][C:7]1[C:2]([CH:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:16]#[N:17])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8794PhenylacetonitrileHCID 8857Ethyl AcetateHCID 8171022,3-DibromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 70979221HCID 70979221, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,3-Dibromo-pyridine (1 eq., 0.5 g) and Phenyl-acetonitrile (4 eq., 0.97 mL) were mixed in NMP (3 mL). Potassium tert-butoxide (1.3 eq, 0.3 g) was added to the solution. The resulting mixture was heated in microwave at 110° C. for 40 min EtOAc and water were added to the reaction mixture. The aqueous layer was separated and extracted with EtOAc (×3). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title compound as a yellow solid. It was used in the next step without further purification

Workup

  1. additionwere added to the reaction mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c20c8f7598164ef797bfc7253dbc78fd
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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