Nitrogen → HCID 86666717, compound

HRID 2401351Notes

Reaction equation

HRID 2401351 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].Br[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].N#N.Cl[CH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[O:21][N:20]=1>CC(N(C)C)=O.O.[Pd](Cl)Cl>[C:1]([O:4][CH2:18][C:19]1[C:23]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[O:10])=[C:22]([CH3:24])[O:21][N:20]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 947NitrogenHCID 811292-BromobenzaldehydeHCID 517044Potassium AcetateHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazole

Product 1

HCID 86666717HCID 86666717, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a resealable vial was added palladium(II) chloride (4.49 mg, 0.025 mmol), potassium acetate (1.24 g, 12.7 mmol), and 2-bromobenzaldehyde (0.59 mL, 5.07 mmol). The vial was sealed and evacuated/backfilled with N2 (3×) before addition of 3-(chloromethyl)-5-methylisoxazole (1.00 g, 7.60 mmol) as a solution in DMA (25 mL). The vial was then heated to 130° C. overnight. The reaction was cooled to room temperature and diluted with water. The solution was extracted with ether 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 (4-(2-formylphenyl)-5-methylisoxazol-3-yl)methyl acetate (1.01 g, 3.90 mmol). LC/MS m/z 260 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-bdc944181581465aa053e0a8095a0a4c
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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