Potassium Carbonate → 5-(3-Fluorophenylethynyl)-pyridine-3-carbaldehyde O-methyloxime

HRID 606873Notes

Reaction equation

HRID 606873 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH:16]=O)[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[O:19]([NH2:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:20][O:19][N:21]=[CH:16][C:12]1[CH:13]=[N:14][CH:15]=[C:10]([C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 860764545-(3-Fluorophenylethynyl)-pyridine-3-carbaldehyde

Product 1

HCID 860764615-(3-Fluorophenylethynyl)-pyridine-3-carbaldehyde O-methyloximeYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 5-(3-fluorophenylethynyl)-pyridine-3-carbaldehyde, (prepared essentially as described in EXAMPLE 89), (90 mg, 0.38 mmol) and methoxylamine hydrochloride (160 mg, 3.02 mmol) and potassium carbonate (260 mg, 1.89 mmol) in ethanol at 80° C. overnight. Cool to room temperature, filter solids and concentrate. Purify the residue by silica gel chromatography, eluting with 5:45:45 ethyl acetate:chloroform:hexanes, to give the title compound as a white solid (45 mg, 47%).

Workup

  1. temperatureHeat
  2. custom(prepared essentially
  3. customat 80° C.
  4. customovernight
  5. filtrationfilter solids
  6. concentrationconcentrate
  7. customPurify the residue by silica gel chromatography
  8. washeluting with 5:45:45 ethyl acetate

Sources & evidence

ORD record
ord-21770dc5aa0e452fb5168ef4e71d642a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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