Triethylamine → HCID 57425441, compound

HRID 1823290Notes

Reaction equation

HRID 1823290 reaction equation
[F:1][C:2]1[C:3]([CH:8]=[N:9][OH:10])=[N:4][CH:5]=[CH:6][CH:7]=1.ClN1C(=O)CCC1=O.[CH2:19]([O:21][C:22](=[O:26])[C:23]#[C:24][CH3:25])[CH3:20].C(N(CC)CC)C>CN(C)C=O.C(OCC)C.C(OCC)(=O)C.O>[CH2:19]([O:21][C:22]([C:23]1[C:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:9][O:10][C:24]=1[CH3:25])=[O:26])[CH3:20]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 78043Ethyl 2-butynoateHCID 136359763HCID 136359763, compound

Product 1

HCID 57425441HCID 57425441, compoundYield 11.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-fluoropyridine-2-carboxaldehyde oxime (2.55 g, 0.018 mol) in N,N-dimethylformamide (20 mL). Add N-chlorosuccinimide (2.71 g, 0.02 mol) in small portions and stir for 6 h at ambient temperature. Pour into water and extracte with ethyl acetate. Wash the combined extracts with water and dry over sodium sulfate. Concentrate in vacuo to give crude product. Use without further purification. MS(FD): M+ 174.0, 175.9 m/z. Combine this material with ethyl-2-butynoate (5.30 mL, 0.046 mol) in diethyl ether (200 mL) under a nitrogen atmosphere. Add triethylamine (3.29 mL, 0.024 mol) in a dropwise manner and stir over a weekend at ambient temperature. Quench the mixture with water and extract with ethyl acetate. Dry the combined extracts over sodium sulfate and concentrate. Elute over silica gel with methanol/dichloromethane to give the desired isoxazole (0.52 g, 11%). ES(ES): (M+1)+ 251.0, 252.0 m/z.

Workup

  1. washWash the combined extracts with water
  2. dry with materialdry over sodium sulfate
  3. concentrationConcentrate in vacuo
  4. customto give crude product
  5. customUse without further purification
  6. customQuench the mixture with water
  7. extractionextract with ethyl acetate
  8. dry with materialDry the combined extracts over sodium sulfate
  9. concentrationconcentrate
  10. washElute over silica gel with methanol/dichloromethane

Sources & evidence

ORD record
ord-0256602bf29840e09a755832581986bf
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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