Potassium Carbonate → HCID 86704500, compound

HRID 633401Notes

Reaction equation

HRID 633401 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19]1[C:22]2([CH2:25][NH:24][CH2:23]2)[CH2:21][O:20]1>CN(C)C=O.O>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:24]2[CH2:25][C:22]3([CH2:19][O:20][CH2:21]3)[CH2:23]2)=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 231118872-Oxa-6-azaspiro[3.3]heptane

Product 1

HCID 86704500HCID 86704500, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-5-nitrobenzonitrile (1.0 g, 6.02 mmol, purchased from Combi-Blocks AN1040) was dissolved in dimethylformamide (25 mL) under nitrogen. Potassium carbonate (3.50 g, 25.3 mmol) and 2-oxa-6-azaspiro[3.3]heptane (1.05 g, 7.22 mmol, purchased from Ryan Scientific EN300-89755) were added to the mixture. The resulting mixture was stirred at room temperature overnight. The reaction was then diluted with water (75 mL) and extracted with ethyl acetate (4×75 mL). The organic layer was washed with water (5×75 mL) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by Combiflash, eluting with hexane and ethyl acetate to provide the desired product as a bright yellow solid (350 mg, 24% yield).

Workup

  1. extractionextracted with ethyl acetate (4×75 mL)
  2. washThe organic layer was washed with water (5×75 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by Combiflash
  7. washeluting with hexane and ethyl acetate

Sources & evidence

ORD record
ord-850e11a9f7414d3faa64d7974740ed42
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

Loading…