Chloroform → HCID 67047974, compound

HRID 606927Notes

Reaction equation

HRID 606927 reaction equation
Cl.[C:2]1([C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH:16]=[N:17]O)[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)(Cl)Cl.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>[Zn]>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[C:2]1([C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH2:16][NH2:17])[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 866224835-Phenylethynylpyridine-3-carbaldehyde oxime hydrochloride

Product 2

HCID 6422Trifluoroacetic acidYield 0.02%HCID 67047974HCID 67047974, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Add zinc dust (0.39 g, 6.04 mmol) in small portions to a solution of 5-phenylethynyl-pyridine-3-carbaldehyde oxime hydrochloride, (prepared as described in EXAMPLE 6), (0.16 g, 0.60 mmol) in trifluoroacetic acid (1.4 mL) while keeping the internal reaction temperature between about 15-20° C. using a chilled water bath. After 15 min, add a 1:1 mixture of 2 N sodium hydroxide and chloroform, while stirring vigorously and cooling in an ice bath. Filter away the solids and wash the filtrate with water, an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by reverse phase HPLC, eluting with 5:95 to 100:0 acetonitrile:water with 0.02% trifluoroacetic acid, to give the title compound as pale yellow solid (0.015 g, 11.9%).

Workup

  1. custombetween about 15-20° C.
  2. additionadd
  3. temperaturecooling in an ice bath
  4. filtrationFilter away the solids
  5. washwash the filtrate with water
  6. dry with materialan aqueous saturated solution of sodium chloride, dry (magnesium sulfate)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the residue by reverse phase HPLC
  10. washeluting with 5:95 to 100:0 acetonitrile

Sources & evidence

ORD record
ord-4973aa4cd8ef455ebaa4b6536b521f71
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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