HCID 69673559, compound → HCID 86695672, compound

HRID 2283252Notes

Reaction equation

HRID 2283252 reaction equation
CO[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[C:15]2[O:16][CH:17]=[C:18]([C:20]([O:22]C)=O)[N:19]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:30][Mg+].[Br-]>C1COCC1>[C:5]1([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[C:15]2[O:16][CH:17]=[C:18]([C:20](=[O:22])[CH3:30])[N:19]=2)[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 69673559HCID 69673559, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86695672HCID 86695672, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 26 (50 mg, 0.14 mmol) in THF (4 mL), MeMgBr (0.7 mL, 0.70 mmol) was added at −40° C. and the reaction mixture was warmed to rt and stirred for 1 h. The reaction mixture was quenched by addition of saturated ammonium chloride solution, extracted with ethyl acetate (25 mL), washed with brine (1×10 mL) and dried over Na2SO4. Evaporation of the solvent under reduced pressure gave the crude product which was purified by column chromatography (100-200 mesh silica gel, 20% EtOAc-hexane) to furnish 1-(2-(3,5-diphenylpyridazin-4-yl)oxazol-4-yl)ethanone (20 mg, 42%) as an off white solid.

Workup

  1. customThe reaction mixture was quenched by addition of saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (25 mL)
  3. washwashed with brine (1×10 mL)
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent under reduced pressure
  6. customgave the crude product which
  7. customwas purified by column chromatography (100-200 mesh silica gel, 20% EtOAc-hexane)

Sources & evidence

ORD record
ord-eaec8738402249ca8b69b0b343eab93e
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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