Nitrogen → HCID 67815348, compound

HRID 2401341Notes

Reaction equation

HRID 2401341 reaction equation
C([O-])(=O)C.[K+].Br[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10].N#N.[CH3:17][O:18][C:19]1[CH:33]=[CH:32][C:22]([CH2:23][O:24][CH2:25][C:26]2[CH:30]=[C:29]([CH3:31])[O:28][N:27]=2)=[CH:21][CH:20]=1>O.[Pd](Cl)Cl.CC(N(C)C)=O>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][O:24][CH2:25][C:26]2[C:30]([C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[C:9]#[N:10])=[C:29]([CH3:31])[O:28][N:27]=2)=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 162722-BromobenzonitrileHCID 517044Potassium AcetateHCID 67814067HCID 67814067, compound

Product 1

HCID 67815348HCID 67815348, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a resealable vial was added potassium acetate (112 mg, 1.143 mmol), palladium(II) chloride (0.507 mg, 2.86 μmol), and 2-bromobenzonitrile (104 mg, 0.572 mmol). The vial was sealed and evacuated and purged with N2 (3×) before addition of DMA (4 mL) and 3-((4-methoxybenzyloxy)methyl)-5-methylisoxazole (200 mg, 0.857 mmol). The vial was heated to 130° C. overnight. The reaction was cooled to room temperature and diluted with water. The aqueous was extracted with EtOAc and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)benzonitrile. LC/MS m/z 335 [M+H]+.

Workup

  1. customThe vial was sealed
  2. customevacuated
  3. temperatureThe reaction was cooled to room temperature
  4. extractionThe aqueous was extracted with EtOAc
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-0e22af52403e43d3badc2b41b90542e0
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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