HCID 59390004, compound → HCID 68459644, compound

HRID 2358559Notes

Reaction equation

HRID 2358559 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[N:3]=1.[CH2:15]([Mg]Cl)[CH:16]([CH3:18])[CH3:17]>C1COCC1.CN1C(=O)CCC1>[CH3:14][C:9]1[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:3]=2)[C:12]([CH3:13])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 59390004HCID 59390004, compoundHCID 178418368HCID 178418368, compound

Product 1

HCID 68459644HCID 68459644, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product from Example 12b (1.0 g, 4.84 mmol) was treated with 2.0 M isobutylmagnesium chloride (2.90 mL, 5.81 mmol) in 30 mL THF and 3 mL NMP at room temperature under a N2 atmosphere. Added Fe(acac)3 (85 mg, 0.242 mmol) and stirred at room temperature for 18 h. During the course of the reaction two additional charges of Grignard reagent and catalyst were added. The reaction was quenched by pouring into 5% acetic acid and extracting with ether. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound that was purified by silica gel column chromatography eluting with 10% EtOAc/hexane to give (620 mg, 56%).

Workup

  1. additionwere added
  2. customThe reaction was quenched
  3. additionby pouring into 5% acetic acid
  4. extractionextracting with ether
  5. dry with materialDried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-00dfd63603ea415889f9bcd93966815c
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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